m-Chloroperbenzoic acid → HCID 58392148, compound

HRID 561569Notes

Reaction equation

HRID 561569 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:17]1[C:25]2[C:20](=[C:21]([CH2:26][S:27][CH3:28])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[CH2:13][CH2:14][C:15]#[N:16].ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]([C:17]1[C:25]2[C:20](=[C:21]([CH2:26][S:27]([CH3:28])=[O:37])[CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[CH2:13][CH2:14][C:15]#[N:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58392279HCID 58392279, compound

Product 1

HCID 58392148HCID 58392148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg of the compound from Example 47 with a purity of 85% (0.21 mmol) were introduced into 14 ml of dichloromethane at 0° C., 59.1 mg (0.24 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 62 mg (71% 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-519af767a0144370a7d0a55289e60419
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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