Thiophenol → [4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride

Reaction equation

[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH2:35][CH2:36][S:37][CH3:38])[NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@@H:16]2[CH2:20][S:19][CH2:18][N:17]2C(OC(C)(C)C)=O)=[O:15])=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(S)C=CC=CC=1.[ClH:47].O1CCOCC1>>[ClH:47].[CH3:1][O:2][C:3](=[O:39])[C@H:4]([CH2:35][CH2:36][S:37][CH3:38])[NH:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@@H:16]2[CH2:20][S:19][CH2:18][NH:17]2)=[O:15])=[CH:9][C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 3

HCID 7969Thiophenol

HCID 204431481,4-Dioxane hydrochloride

HCID 54440271[4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester

Product 1

HCID 70212058[4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride

Procedure

To a mixture of [4-(N-tert-butoxycarbonyl-(R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester (270 mg, 0.47 mmol) and thiophenol (0.1 mL, 0.97 mmol) was added 4N HCl-dioxane (10 mL) and the reaction mixture was stirred for 45 minutes at ambient temperature. The reaction mixture was partitioned between water and ether. The aqueous phase was extracted with ether. The organic extracts were discarded and the aqueous phase was lyophilized to give [4-((R)-thiazolidin-4-ylcarbonyl)amino-2-phenylbenzoyl]methionine methyl ester hydrochloride (150 mg).