Dichloromethane → HCID 58392150, compound

HRID 561624Notes

Reaction equation

HRID 561624 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:11][C:12]#[N:13])=[C:4]([F:26])[CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:38])C=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([F:26])[C:5]([CH:9]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:38])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:11][C:12]#[N:13])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392264HCID 58392264, compound

Product 1

HCID 58392150HCID 58392150, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

231 mg (0.59 mmol) of the compound from Example 153 were introduced into 40 ml of dichloromethane at 0° C., 198 mg (0.81 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at 0° C. for 2 h. 2 ml of methanol were added, and the solution was concentrated. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, and the solvents were removed in a rotary evaporator. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) to result in 171 mg (71% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationthe solution was concentrated
  2. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. customthe solvents were removed in a rotary evaporator
  4. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-35a7c80aa84d46eaa77785e013971fb6
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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