Dichloromethane → HCID 58392113, compound

HRID 561570Notes

Reaction equation

HRID 561570 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([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)[CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[CH:4][CH:3]=1.ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:14]2[C:22]3[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:37])[CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:9][CH2:10][CH2:11][C:12]#[N:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392514HCID 58392514, compound

Product 1

HCID 58392113HCID 58392113, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 mg (0.14 mmol) of the compound from Example 49 were introduced into 9 ml of dichloromethane while cooling in ice, 33.4 mg (0.14 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 and saturated aqueous sodium bicarbonate solution, the phases were separated, the organic phase was 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 33 mg (63% of theory) of the title compound as mixture of diastereomers.

Workup

  1. temperaturewhile cooling in ice
  2. concentrationthe residue after concentration
  3. customsaturated aqueous sodium bicarbonate solution, the phases were separated
  4. washthe organic phase was washed twice with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. 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-7a210874d3d94628b1596d21f191b709
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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