m-Chloroperbenzoic acid → HCID 58392503, compound

HRID 561567Notes

Reaction equation

HRID 561567 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:23][S:24][CH3:25])[CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:13]2[C:21]3[C:16](=[C:17]([CH2:23][S:24]([CH3:25])=[O:34])[CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58392535HCID 58392535, compound

Product 1

HCID 58392503HCID 58392503, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64.0 mg (0.17 mmol) of the compound from Example 43 were introduced into 10 ml of dichloromethane at 0° C., 42.3 mg (0.17 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 54 mg (79% 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-18dba7279ca14a7e836326c7307291fe
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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