Dichloromethane → HCID 58392159, compound

HRID 561625Notes

Reaction equation

HRID 561625 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)([CH2:13][CH3:14])[CH2:9][CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:38])C=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:15]2[C:23]3[C:18](=[C:19]([CH2:24][S:25]([CH3:26])=[O:38])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)([CH2:13][CH3:14])[CH2:9][CH2:10][C:11]#[N:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392372HCID 58392372, compound

Product 1

HCID 58392159HCID 58392159, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120 mg (0.31 mmol) of the compound from Example 157 were introduced into 12 ml of dichloromethane at 0° C., 77 mg (0.31 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT for 2 h. 2 ml of methanol were added and the solution was concentrated. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 120 mg (96% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationthe solution was concentrated
  2. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-214564e362b34c15b149d6997cb8188f
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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