Dichloromethane → HCID 58392434, compound

HRID 561623Notes

Reaction equation

HRID 561623 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]([CH2:22][S:23][CH3:24])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[CH:4][C:3]=1[F:25].ClCCl.ClC1C=CC=C(C(OO)=[O:37])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]([CH2:22][S:23]([CH3:24])=[O:37])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[CH:4][C:3]=1[F:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392114HCID 58392114, compound

Product 1

HCID 58392434HCID 58392434, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 mg (0.81 mmol) of the compound from Example 152 were introduced into 55 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 RT 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 266 mg (85% 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-4d06b880e1284335ac02e6abad5bd8fd
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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