Dichloromethane → HCID 58392267, compound

HRID 561565Notes

Reaction equation

HRID 561565 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:14]1[C:22]2[C:17](=[C:18]([CH2:23][S:24][CH3:25])[CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH2:10][CH2:11][C:12]#[N:13].ClCCl.ClC1C=CC=C(C(OO)=[O:37])C=1>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:14]1[C:22]2[C:17](=[C:18]([CH2:23][S:24]([CH3:25])=[O:37])[CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[CH2:10][CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 59293937HCID 59293937, compound

Product 1

HCID 58392267HCID 58392267, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

200 mg (0.51 mmol) of the compound from Example 41 were introduced into 30 ml of dichloromethane at 0° C., 127 mg (0.51 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 99 mg (48% 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-4ca127cace71445abbfa5519d9cf3da1
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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