Oxalyl chloride → (+/-)-8-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]octanoic acid, methyl ester

HRID 1440080Notes

Reaction equation

HRID 1440080 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][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].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][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic AcidHCID 12878164Methyl 8-aminooctanoate hydrochloride

Product 1

HCID 14155014(+/-)-8-[[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]amino]octanoic acid, methyl ester

Procedure

2-Acetylthiomethyl-3-phenylpropanoic acid is reacted with oxalyl chloride and the resulting acid chloride is then reacted with 8-aminooctanoic acid, methyl ester hydrochloride in the presence of diisopropylethylamine as more fully described in Example 11 of European Patent Application 136,883 to give (±)-8-[[2-[(acetylthio)methyl]-1-oxo-3phenylpropyl]amino]octanoic acid, methyl ester.

Sources & evidence

ORD record
ord-eb3592faf72240fa98a5113c44381ecc
Source dataset
uspto-grants-1996_03
Patent number
US05496805

Reaction notes

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