m-Chloroperbenzoic acid → HCID 58392522, compound

HRID 561566Notes

Reaction equation

HRID 561566 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:14]1[C:22]2[C:17](=[C:18]([CH2:24][S:25][CH3:26])[CH:19]=[C:20]([F:23])[CH:21]=2)[NH:16][CH:15]=1)[CH2:10][CH2:11][C:12]#[N:13].ClC1C=CC=C(C(OO)=[O:35])C=1>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:14]1[C:22]2[C:17](=[C:18]([CH2:24][S:25]([CH3:26])=[O:35])[CH:19]=[C:20]([F:23])[CH:21]=2)[NH:16][CH:15]=1)[CH2:10][CH2:11][C:12]#[N:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58392100HCID 58392100, compound

Product 1

HCID 58392522HCID 58392522, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.25 mmol) of the compound from Example 42 were introduced into 14 ml of dichloromethane at 0° C., 60.5 mg (0.25 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. It was concentrated, and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 80 mg (76% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationIt was concentrated
  2. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record
ord-883468ea6b084aa1967d12f151eff6f1
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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