Thiophenol → HCID 66918859, compound

Reaction equation

[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]([O:12][C:13]([C@@H:15]1[CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17][C@H:16]1[C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[O:26])=[O:14])[CH3:11]>C1COCC1>[CH2:10]([O:12][C:13]([C@@H:15]1[CH2:19][C@@H:18]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:17][C@H:16]1[C:25]([N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)=[O:26])=[O:14])[CH3:11]

Participants

Procedure

To a solution of the thiophenol (0.41 mmol) in THF (4 ml) was added NaH (55% in oil, 0.41 mmol) at 22° C. and stirring was continued until gas evolution ceased. To the mixture was added a solution of (1R,2R,4R)-4-methanesulfonyloxy-2-(morpholine-4-carbonyl)-cyclopentanecarboxylic acid ethyl ester (0.28 mmol) in THF (4 ml) and stirring was continued at 50° C. until completion of the reaction. The mixture was partitioned between ethyl acetate and water, the organic layer was dried, evaporated and the residue chromatographed on silica using mixtures of cyclohexane and ethyl acetate to give the title compound as pale yellow oil. MS: 364.5 (M+H)+.