m-Chloroperbenzoic acid → HCID 70287772, compound
Reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([N:13]1[C@H:17]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH2:16][S:15][CH2:14]1)=[O:12].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][C:11]([N:13]1[C@H:17]([C:18]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[O:19])[CH2:16][S:15](=[O:33])[CH2:14]1)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Dissolved in 100 ml of chloroform were 5 g of 3-(2-indanacetyl)-4(R)-(1-pyrrolidinecarbonyl)thiazolidine (a compound according to Preparation Example 2 set forth in Japanese Patent Application Laid-Open No. 262557/1990). While chilling with ice water, 3.3 g of meta-chloro-perbenzoic acid were gradually added to the solution. After stirring the mixture for 3 hours, the resultant liquid reaction mixture was washed successively with a 5% solution of sodium thiosulfate and a saturated aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:chloroform=5:95), thereby obtaining 3.8 g of the title compound as a diastereomeric mixture. Yield: 73%.