m-Chloroperbenzoic acid → HCID 69853689, compound

HRID 987912Notes

Reaction equation

HRID 987912 reaction equation
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH:12]([O:14][CH3:15])[CH2:11][CH2:10][CH:9]1[CH2:16][CH:17]([OH:47])[CH:18]([NH:26][C:27](=[O:46])[CH:28]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:29][S:30][C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:56])C=1>ClCCl>[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH:12]([O:14][CH3:15])[CH2:11][CH2:10][CH:9]1[CH2:16][CH:17]([OH:47])[CH:18]([NH:26][C:27](=[O:46])[CH:28]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH2:29][S:30]([C:31]1[CH:40]=[CH:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=1)=[O:56])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69853770HCID 69853770, compound

Product 1

HCID 69853689HCID 69853689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of 2-{2-Hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-ylsulfanyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide (80 mg, 0.117 mmol) in dichloromethane (3 ml) was cooled to −10° C. A solution of meta-chloroperbenzoic acid in dichloromethane (2 ml) was added and the mixture stirred at −10° C. for 30 minutes. The solution was then washed with 5% aqueous sodium hydrogen carbonate solution, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel (dichloromethane/methanol: 97/3 2-{2-Hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-sulfinyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide (65 mg, 70%) as a white solid. Mass spectrum, 701 [M+H]+. The following compounds were prepared in a similar manner, by oxidation of the appropriate sulphide:

Workup

  1. washThe solution was then washed with 5% aqueous sodium hydrogen carbonate solution
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customto give
  5. customafter purification by flash chromatography on silica gel (dichloromethane/methanol
  6. customThe following compounds were prepared in a similar manner, by oxidation of the appropriate sulphide

Sources & evidence

ORD record
ord-bcf2727ebaa54c63b2b80585ea8cc5a6
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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