Ammonium Chloride → (R)-4-(3-Hydroxy-1-oxopropyl)-3-[[(S)-1-(phenylmethyloxycarbonyl)-2-pyrrolidinyl]carbonyl]thiazolidine
Reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])=[O:12])(C(C)(C)C)(C)C.[Cl-].[NH4+]>C(O)(=O)C.C1COCC1.O>[OH:8][CH2:9][CH2:10][C:11]([C@@H:13]1[CH2:17][S:16][CH2:15][N:14]1[C:18]([C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:19])=[O:12]Participants
4
Procedure
(R)-4-[3-(tert-Butyldimethylsilyloxy)-1-oxopropyl]-3-[[(S)-1-(phenylmethyloxycarbonyl)-2-pyrrolidinyl]carbonyl]thiazolidine (215 mg) was dissolved in a mixture of acetic acid-THF-water (3:1:1, 3 ml), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into saturated ammonium chloride and extracted with chloroform. The organic layer was washed with water, saturated sodium hydrogencarbonate and saturated brine in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by preparative thin-layer chromatography (silica gel, developing solvent: chloroform-methanol) to give the title compound (97 mg) (see Table 5).