Dichloromethane → HCID 58392181, compound

HRID 561564Notes

Reaction equation

HRID 561564 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])=[C:4]([F:26])[CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:38])C=1>CO>[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])=[O:38])[CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[C:4]([F:26])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392204HCID 58392204, compound

Product 1

HCID 58392181HCID 58392181, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

80.0 mg (0.21 mmol) of the compound from Example 40 were introduced into 5 ml of dichloromethane at 0° C., 53.0 mg (0.22 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. Methanol was added, and the residue after concentration was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 58.8 mg (71% 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 of 0.1% formic acid)

Sources & evidence

ORD record
ord-3304d0941669421997e65ed16822fa54
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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