Dichloromethane → HCID 58392494, compound

HRID 561563Notes

Reaction equation

HRID 561563 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])=[C:4]([F:25])[CH:3]=1.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])=[C:4]([F:25])[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392400HCID 58392400, compound

Product 1

HCID 58392494HCID 58392494, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg (0.54 mmol) of the compound from Example 38 were introduced into 30 ml of dichloromethane at 0° C., 132 mg (0.54 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT overnight. 2 ml of methanol were added, and the residue after concentration was taken up in dichloromethane, washed twice with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 107 mg (51% of theory) of the title compound as mixture of diastereomers.

Workup

  1. concentrationthe residue after concentration
  2. washwashed twice with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. 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-6eea698a15f44b54bb939a71e37a726e
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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