m-Chloroperbenzoic acid → HCID 58392342, compound

HRID 561561Notes

Reaction equation

HRID 561561 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)[CH2:14][CH2:15][C:16]#[N:17].ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[CH3:1][S:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]([C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=1)[CH2:14][CH2:15][C:16]#[N:17])=[O:36]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58392446HCID 58392446, compound

Product 1

HCID 58392342HCID 58392342, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 mg (64 μmol) of the compound from Example 35 were introduced into 5 ml of dichloromethane at 0° C., 16 mg (64 μmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. The residue after concentration was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient with addition to 0.1% formic acid) to result in 24 mg (92% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationThe residue after concentration
  2. customwas purified by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient with addition to 0.1% formic acid)

Sources & evidence

ORD record
ord-fadebb8ef62146ea9f49605519e37624
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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