m-Chloroperbenzoic acid → HCID 69853707, compound

HRID 987913Notes

Reaction equation

HRID 987913 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:48])[CH:18]([NH:26][C:27](=[O:47])[CH:28]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH2:29][S:30]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=1)=[O:31])[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:57])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:48])[CH:18]([NH:26][C:27](=[O:47])[CH:28]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH2:29][S:30]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=1)(=[O:57])=[O:31])[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 69853689HCID 69853689, compound

Product 1

HCID 69853707HCID 69853707, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-{2-hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-sulfinyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide in dichloromethane (2 ml) was treated with a solution of meta-chloroperbenzoic acid (13 mg) in dichloromethane (1 ml) and the reaction mixture stirred at room temperature for 2 hours. The solution was then washed with 5% aqueous sodium hydrogen carbonate solution, dried (anhydrous magnesium sulfate) and concentrated in vacuo to give 2-{2-hydroxy-3-[2-methanesulfonylamino-3-(naphthalen-2-sulfonyl)-propionylamino]-4-phenyl-butyl}-5-methoxy-cyclohexanecarboxylic acid tert-butylamide (23 mg, 92%) as a white foam. Mass spectrum, 717 [M+H]+.

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

Sources & evidence

ORD record
ord-60a9232c0b8445ab90ad851d266fd995
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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