Oxalyl chloride → (+/-)-4-[[2-[(Acetylthio)methyl]-1 oxo-3-phenylpropyl]amino]butanoic acid, methyl ester

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Reaktionsgleichung

[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=O)(=[O:3])[CH3:2].C(Cl)(=O)C(Cl)=O.Cl.[NH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(N(C(C)C)CC)(C)C>>[C:1]([S:4][CH2:5][CH:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([NH:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:9])(=[O:3])[CH3:2]

Komponenten

Edukt 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 27563834-Aminobutyric acid methyl ester hydrochloride

HCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid

Produkt 1

HCID 13477463(+/-)-4-[[2-[(Acetylthio)methyl]-1 oxo-3-phenylpropyl]amino]butanoic acid, methyl ester

Versuchsvorschrift

2-Acetylthiomethyl-3-phenylpropanoic acid is reacted with oxalyl chloride and the resulting acid chloride is then reacted with 4-aminobutanoic acid, methyl ester, hydrochloride in the presence of diisopropylethylamine as more fully described in Example 2 of European Patent Application 136,883 to give (±)-4-[[2-[(acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]butanoic acid, methyl ester.

Quellen und Nachweise

ORD-Eintrag: ord-5d15dcb2d34147eea3938b984c27c0aa
Quelldatensatz: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05496805

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