Category: 65090-78-0

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of hydroxyamino acids and N-methyl derivatives. III. Synthesis of DL-serine and N-methylserine》. Authors are Izumiya, Nobuo.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Name: 2-Bromo-3-methoxypropanoic acid. Through the article, more information about this compound (cas:65090-78-0) is conveyed.

cf. C.A. 45, 4656e. Exptl. procedures for the synthesis of DL-serine and N-methylserine from CH2:CHCO2H (I) are described. I (14.4 g.) added to 14 g. Hg(OAc)2 in 300 cc. of MeOH, and gave after 2 days 54 g. α-acetoxymercuri-β-methoxypropionic acid, m. 200-4°; to this in 200 cc. water and 36 g. KBr, in direct sunlight, was added dropwise 32 g. Br and 36 g. KBr in 60 cc. water; extraction of the mixture with ether after addition of 33 cc. 48% HBr gave 37 g. crude α-bromo-β-methoxypropionic acid (II), b4 92-5°. Aqueous NH3 with 37 g. II gave the α-amino acid (III), decompose 233-4°, in 34% yield (based on I); Cu salt, C8H16O6N2Cu, scarcely soluble in water; phenylurea, MeOCH2CH(NHCONHPh)CO2H, m. 171-2°; N-(p-tolylsulfonyl) derivative (IV), m. 139-41°. Serine was obtained by boiling crude III with 48% HBr (yield 41%, based on I). Heating IV with MeI and 2 N NaOH 1 hr. in a sealed tube at 70° gave β-methoxy-α-[methyl(p-tolylsulfonyl)amino]propionic acid (V), C12H17O5NS, m. 92°. Heating crude 3.7 g. II and 35% 9 cc. MeNH2 4 hrs. in a sealed tube at 100° gave 0.74 g. β-methoxy- α-(methylamino)propionic acid (VI), m. 233° (decomposition); picrolonate, C15H19O8N5, m. 120-1° (decomposition); Cu salt, C10H20O6N2Cu.3H2O, m. 234° (decomposition). The crude product from II and MeNH2 gave with 48% HBr N-methylserine, m. 203-4° (decomposition), 30% yield (based on I); picrolonate, C14H17O8N5, m. 130-4° (decomposition); Cu salt, C8H16O6N2Cu, m. 197-8° (decomposition). VI was also obtained by hydrolysis of V with concentrated HCl.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Attempted synthesis of polypeptides by condensation of amino acid and peptide esters I, published in 1954, which mentions a compound: 65090-78-0, mainly applied to , Synthetic Route of C4H7BrO3.

Methods are given for fractionation of the amino acid, peptides, and their Me esters in the cases of glycine (I), alanine (II), and serine (III). After several months at room temperature, either dry or in various solvents, I Me ester gave mainly tetraglycine Me ester (IV) and I anhydride (V), as well as some pentaglycine Me ester and hexaglycine Me ester. In H2O, MeOH, or EtOH the product was mostly V. Condensation of II Me ester, either dry or in MeOH, gave mainly II anhydride. In H2O hydrolysis to II occurred. III Me ester (VI), dry or in various solvents at 20°, gave after several weeks mainly III anhydride (VII), with some III and unchanged VI. Vacuum distillation of VI gave VII, III, MeOH, NH3, H2O, II, and traces of III peptides. VI was kept in vacuo at 20°, warmed 1 h. to 75°, refluxed 10 h., or kept at 20° in pyridine or HOAc. In each case the major product was VII, and III, VI, and some III peptides were present. IV kept at various temperatures, dry or in H2O or MeOH, was either unchanged, hydrolyzed, or converted largely to unidentified products.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《β-Amino acids. IV. β-Methionine and β-ethionine》. Authors are Birkofer, Leonhard; Storch, Ingeborg.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Safety of 2-Bromo-3-methoxypropanoic acid. Through the article, more information about this compound (cas:65090-78-0) is conveyed.

cf. C.A. 49, 2317d. HO2CCHAcCH2CO2Et and NaH gave the Na salt, which with ClCH2SMe yielded EtO2CAc(CH2SMe)CH2CO2Et (I), b3 153° (2,4-dinitrophenylhydrazone, m. 92-3°). Refluxed 10 hrs. with 18% HCl I gave AcCH(CH2SMe)CH2CO2H, isolated as the Et ester (II), b3 123° (2,4-dinitrophenylhydrazone, m. 62-3°), as well as AcC(:CH2)CH2CO2H (2,4-dinitrophenylhydrazone, m. 210°), and 3-acetyl-γ-butyrolactone (2,4-dinitrophenylhydrazone, m. 193°). I refluxed with HCl only 4 hrs. gave mono-Et 2-acetyl-2-(methylthiomethyl)succinate, b0.001 115-17° (2,4-dinitrophenylhydrazone, m. 169-70°). I was saponified with Ba(OH)2 to HO2CCH(CH2SMe)CH2CO2H, m. 114-15°. II and HN3 in the presence of HCl gave β-methionine (III), m. 197-8° (picrolonate, m. 190-2°; 3,5-dinitrobenzoyl derivative, m. 200°). MeSCH2CH:CHCO2H, m. 58.5°, obtained from MeSCH2CHO and CH2(CO2H)2 (IV), gave III with NH3 in a sealed tube at 150-60°. EtSNa, obtained from EtSH with Na, and bromoacetal gave EtSCH2CH(OEt)2, converted by HCl to the aldehyde, b14 45-6°, which with IV gave EtSCH2CH:CHCO2H, which with NH3 in a sealed tube yielded β-ethionine (V), m. 198° (picrolonate, m. 180-3°). III and V do not react with aqueous ninhydrin, but give a blue color with it in 95% BuOH-5% 2N HOAc.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Safety of 2-Bromo-3-methoxypropanoic acid. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Bromo-3-methoxypropanoic acid, is researched, Molecular C4H7BrO3, CAS is 65090-78-0, about N-Substituted amino acid N’-benzylamides: synthesis, anticonvulsant, and metabolic activities. Author is Beguin, Cecile; LeTiran, Arnaud; Stables, James P.; Voyksner, Robert D.; Kohn, Harold.

Amino acid amides (AAA) were prepared and evaluated in seizure models. The AAA displayed moderate-to-excellent activity in the maximal electroshock seizure (MES) test and were devoid of activity in the s.c. Metrazol-induced (scMet) seizure test. The AAA anticonvulsant activity was neither strongly influenced by the C(2) substituent nor by the degree of terminal amine substitution. An in vitro metabolism study suggested that the structure-activity relationship pattern was due, in part, to metabolic processes that occurred at the N-terminal amine unit.

From this literature《N-Substituted amino acid N’-benzylamides: synthesis, anticonvulsant, and metabolic activities》,we know some information about this compound(65090-78-0)Safety of 2-Bromo-3-methoxypropanoic acid, but this is not all information, there are many literatures related to this compound(65090-78-0).

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Attempted synthesis of polypeptides by condensation of amino acid and peptide esters I》. Authors are Brockmann, Hans; Musso, Hans.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Computed Properties of C4H7BrO3. Through the article, more information about this compound (cas:65090-78-0) is conveyed.

Methods are given for fractionation of the amino acid, peptides, and their Me esters in the cases of glycine (I), alanine (II), and serine (III). After several months at room temperature, either dry or in various solvents, I Me ester gave mainly tetraglycine Me ester (IV) and I anhydride (V), as well as some pentaglycine Me ester and hexaglycine Me ester. In H2O, MeOH, or EtOH the product was mostly V. Condensation of II Me ester, either dry or in MeOH, gave mainly II anhydride. In H2O hydrolysis to II occurred. III Me ester (VI), dry or in various solvents at 20°, gave after several weeks mainly III anhydride (VII), with some III and unchanged VI. Vacuum distillation of VI gave VII, III, MeOH, NH3, H2O, II, and traces of III peptides. VI was kept in vacuo at 20°, warmed 1 h. to 75°, refluxed 10 h., or kept at 20° in pyridine or HOAc. In each case the major product was VII, and III, VI, and some III peptides were present. IV kept at various temperatures, dry or in H2O or MeOH, was either unchanged, hydrolyzed, or converted largely to unidentified products.

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Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 65090-78-0. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Bromo-3-methoxypropanoic acid, is researched, Molecular C4H7BrO3, CAS is 65090-78-0, about New and alternate synthesis of lacosamide with chemoenzymatic method. Author is Gurunadham, G.; Madhusudhan, Raju R..

Lacosamide [(R)-2-acetamido-N-benzyl-3-methoxy propionamide] 5 is a novel antiepileptic drug. Lacosamide was prepared by a chem. method with enzymic resolution of racemic lacosamide. Herein is reported an expedient four-steps enantioselective synthesis of lacosamide 5 beginning with Me 2,3-dibromo propionate 1. A new resolution process catalyzed by Novozyme 435. The products were obtained in very good yields and in a state of high purity. All the newly synthesized compounds (2-5) were characterized by their spectral (IR, 1H NMR, C13 NMR and MS) data.

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Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《β-Amino acids. IV. β-Methionine and β-ethionine》. Authors are Birkofer, Leonhard; Storch, Ingeborg.The article about the compound:2-Bromo-3-methoxypropanoic acidcas:65090-78-0,SMILESS:O=C(O)C(Br)COC).Safety of 2-Bromo-3-methoxypropanoic acid. Through the article, more information about this compound (cas:65090-78-0) is conveyed.

cf. C.A. 49, 2317d. HO2CCHAcCH2CO2Et and NaH gave the Na salt, which with ClCH2SMe yielded EtO2CAc(CH2SMe)CH2CO2Et (I), b3 153° (2,4-dinitrophenylhydrazone, m. 92-3°). Refluxed 10 hrs. with 18% HCl I gave AcCH(CH2SMe)CH2CO2H, isolated as the Et ester (II), b3 123° (2,4-dinitrophenylhydrazone, m. 62-3°), as well as AcC(:CH2)CH2CO2H (2,4-dinitrophenylhydrazone, m. 210°), and 3-acetyl-γ-butyrolactone (2,4-dinitrophenylhydrazone, m. 193°). I refluxed with HCl only 4 hrs. gave mono-Et 2-acetyl-2-(methylthiomethyl)succinate, b0.001 115-17° (2,4-dinitrophenylhydrazone, m. 169-70°). I was saponified with Ba(OH)2 to HO2CCH(CH2SMe)CH2CO2H, m. 114-15°. II and HN3 in the presence of HCl gave β-methionine (III), m. 197-8° (picrolonate, m. 190-2°; 3,5-dinitrobenzoyl derivative, m. 200°). MeSCH2CH:CHCO2H, m. 58.5°, obtained from MeSCH2CHO and CH2(CO2H)2 (IV), gave III with NH3 in a sealed tube at 150-60°. EtSNa, obtained from EtSH with Na, and bromoacetal gave EtSCH2CH(OEt)2, converted by HCl to the aldehyde, b14 45-6°, which with IV gave EtSCH2CH:CHCO2H, which with NH3 in a sealed tube yielded β-ethionine (V), m. 198° (picrolonate, m. 180-3°). III and V do not react with aqueous ninhydrin, but give a blue color with it in 95% BuOH-5% 2N HOAc.

Here is a brief introduction to this compound(65090-78-0)Safety of 2-Bromo-3-methoxypropanoic acid, if you want to know about other compounds related to this compound(65090-78-0), you can read my other articles.

Reference:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia