m-Chloroperbenzoic acid → 3-Cyclopentyl-2-(4-methanesulfinyl-phenyl)-N-thiazol-2-yl-propionamide

HRID 430201Notes

Reaction equation

HRID 430201 reaction equation
[CH:1]1([CH2:6][CH:7]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:29]>C(Cl)Cl>[CH:1]1([CH2:6][CH:7]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:23])=[O:29])=[CH:20][CH:21]=2)[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 120889163-Cyclopentyl-2-(4-methylsulfanyl-phenyl)-N-thiazol-2-yl-propionamide

Product 1

HCID 223151473-Cyclopentyl-2-(4-methanesulfinyl-phenyl)-N-thiazol-2-yl-propionamideYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution 3-cyclopentyl-2-(4-methylsulfanyl-phenyl)-N-thiazol-2-yl-propionamide (75 mg, 0.216 mmol) in methylene chloride (1 mL) was treated with 3-chloroperoxybenzoic acid (75% grade, 50 mg, 0.216 mmol). The reaction mixture was immediately monitored by thin layer chromatography and the results indicated the immediate absence of starting material. The reaction mixture was partitioned between water and methylene chloride and then washed with a saturated aqueous sodium bicarbonate solution. The organic layer was further washed with water and then dried over magnesium sulfate, filtered, and concentrated in vacuo. Recrystallization from 1/1 hexanes/ethyl acetate afforded 3-cyclopentyl-2-(4-methanesulfinyl-phenyl)-N-thiazol-2-yl-propionamide (25 mg, 32%) as a white solid: mp 170-173° C.; EI-HRMS m/e calcd for C18H22N2O2S2 (M+) 362.1123, found 362.1121.

Workup

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. washThe organic layer was further washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from 1/1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6987bb03c35e4ca2bff5429799f1401f
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

Loading…