m-Chloroperbenzoic acid → HCID 70287772, compound

HRID 850367Notes

Reaction equation

HRID 850367 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

HCID 70297m-Chloroperbenzoic acidHCID 9798234Z-321

Product 1

HCID 70287772HCID 70287772, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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%.

Workup

  1. customaccording to Preparation Example 2
  2. additionwere gradually added to the solution
  3. customthe resultant liquid reaction mixture
  4. washwas washed successively with a 5% solution of sodium thiosulfate
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (methanol:chloroform=5:95)

Sources & evidence

ORD record
ord-dc38d8cd4eb146cca81276f4c7bc9ba8
Source dataset
uspto-grants-2000_01
Patent number
US06017929

Reaction notes

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