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

HRID 1440076Notes

Reaction equation

[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][C:27]([O:29][CH2:30][CH3:31])=[O:28].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][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:9])(=[O:3])[CH3:2]

Participants

Reactant 4

HCID 65578Oxalyl chloride

HCID 81531Diisopropylethylamine

HCID 458475beta-Alanine, ethyl ester, hydrochloride

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

Product 1

HCID 13477460(+/-)-3-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]propanoic acid, ethyl ester

Procedure

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

Sources & evidence

ORD record: ord-456b7b31f9fd4ec19ae6f8946f1d0acd
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496805

Reaction notes

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