ChemicalBook--->CAS DataBase List--->75266-38-5

75266-38-5

75266-38-5 Structure

75266-38-5 Structure
IdentificationBack Directory
[Name]

L-Vinylglycine hydrochloride
[CAS]

75266-38-5
[Synonyms]

L-Vinylglycine hydrochloride
(S)-vinylglycine hydrochloride
(S)-2-AMinobut-3-enoic acid hydrochloride
(2S)-2-aminobut-3-enoic acid hydrochloride
[Molecular Formula]

C4H8ClNO2
[MDL Number]

MFCD01863784
[MOL File]

75266-38-5.mol
[Molecular Weight]

137.565
Chemical PropertiesBack Directory
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[Appearance]

White to off-white Solid
[Optical Rotation]

Consistent with structure
Spectrum DetailBack Directory
[Spectrum Detail]

L-Vinylglycine hydrochloride(75266-38-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

(S)-2-(BENZYLOXYCARBONYLAMINO)-3-BUTENOIC ACID METHYL ESTER

75266-40-9

L-Vinylglycine hydrochloride

75266-38-5

General procedure for the synthesis of (S)-2-aminobut-3-enoic acid hydrochloride from (S)-2-(benzyloxycarbonylamino)-3-butenoic acid methyl ester: (S)-2-(benzyloxycarbonylamino)-3-butenoic acid methyl ester (0.905 g, 3.61 mmol) was suspended in 6 M hydrochloric acid solution (20 mL). The reaction mixture was heated to reflux for 2 hours and subsequently cooled to room temperature. Extraction was partitioned with dichloromethane (DCM) and the aqueous phase was again washed with DCM. After combining the organic phases, the aqueous phase was concentrated under vacuum to give a white solid product. Purification by acetone recrystallization resulted in the white crystalline product (S)-2-aminobut-3-enoic acid hydrochloride in a yield of 0.350 g and 71% yield. The structure of the product was confirmed by 1H-NMR (500 MHz, DMSO-d6): δ 8.32 (2H, broad single peak, NH2), 6.02-6.11 (1H, multiple peaks, CH=CH2), 5.50-5.75 (2H, multiple peaks, CH=CH2), 4.68-4.73 (1H, multiple peaks, CHCO2H).

[References]

[1] Tetrahedron, 1985, vol. 41, # 19, p. 4347 - 4358
[2] Journal of Organic Chemistry, 1980, vol. 45, # 24, p. 4817 - 4820
[3] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 9, p. 1927 - 1930
[4] Tetrahedron Letters, 1984, vol. 25, # 14, p. 1425 - 1428
[5] Patent: US9434762, 2016, B2. Location in patent: Page/Page column 92
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