m-Chloroperbenzoic acid → HCID 66918487, compound

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9](SC2C=CC=CC=2)[CH2:8][C@H:7]1[C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])=[O:5])[CH3:2].Cl[C:27]1[CH:32]=[CH:31][CH:30]=[C:29](C(OO)=O)[CH:28]=1.[OH:37][S:38]([O-:40])=O.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([S:38]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:40])=[O:37])[CH2:8][C@H:7]1[C:18]([N:20]1[CH2:21][CH2:22][O:23][CH2:24][CH2:25]1)=[O:19])=[O:5])[CH3:2]

Participants

Procedure

To a solution of (1R,2R,4S)-2-(morpholine-4-carbonyl)-4-phenylsulfanyl-cyclopentanecarboxylic acid ethyl ester (0.1 mmol) in dichloromethane (1 ml) was added a solution of m-chloroperbenzoic acid (70%, 0.4 mmol) in dichloromethane (2 ml) and stirring was continued at 22° C. until completion of the reaction. The mixture was vigorously shaken with aqueous NaHSO3, the organic layer was washed with aqueous Na2CO3 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 a colorless oil. MS: 396.1 (M+H)+.