Dichloromethane → HCID 58392451, compound

HRID 561571Notes

Reaction equation

HRID 561571 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]([CH2:23][S:24][CH3:25])[C:18]([F:22])=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[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:13]2[C:21]3[C:16](=[C:17]([CH2:23][S:24]([CH3:25])=[O:37])[C:18]([F:22])=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:10][C:11]#[N:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392410HCID 58392410, compound

Product 1

HCID 58392451HCID 58392451, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

300 mg (0.80 mmol) of the compound from Example 50 were introduced into 55 ml of dichloromethane at 0° C., 198 mg (0.80 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 mixture was extracted with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The phases were separated, and the solvents were removed from the organic phase in vacuo. The crude product was purified initially by preparative HPLC (mobile phase: acetonitrile/water gradient) and then by flash chromatography of the resulting, slightly impure product on silica gel (mobile phase: ethyl acetate). 197 mg (63% of theory) of the title compound were obtained as mixture of diastereomers.

Workup

  1. extractionthe mixture was extracted with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. customThe phases were separated
  3. customthe solvents were removed from the organic phase in vacuo
  4. customThe crude product was purified initially by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-f767c0decff84260956b9ec1e69e2c05
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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