m-Chloroperbenzoic acid → HCID 66918487, compound

HRID 1367457Notes

Reaction equation

HRID 1367457 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

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 66918859HCID 66918859, compound

Product 1

HCID 66918487HCID 66918487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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)+.

Workup

  1. customwas continued at 22° C. until completion of the reaction
  2. washthe organic layer was washed with aqueous Na2CO3 and water
  3. customthe organic layer was dried
  4. customevaporated
  5. customthe residue chromatographed on silica using mixtures of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-792cb93146a44baf9f179ee17d163480
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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