Water → HCID 11706662, compound

HRID 1367816Notes

Reaction equation

HRID 1367816 reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:35])[C@@H:8]([NH:22][C@@H:23]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:24]([F:27])([F:26])[F:25])[CH2:9][S:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[C:18]([F:21])([F:20])[F:19])[CH2:5][CH2:4]1)#[N:2].[OH:36]OS([O-])=O.[K+].[OH2:42]>CO>[C:1]([C:3]1([NH:6][C:7](=[O:35])[C@@H:8]([NH:22][C@@H:23]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:24]([F:26])([F:27])[F:25])[CH2:9][S:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[C:18]([F:20])([F:21])[F:19])(=[O:36])=[O:42])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 87221082HCID 87221082, compound

Product 1

HCID 11706662HCID 11706662, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-cyanocyclopropyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-3-(4-trifluoromethyl-pyridin-3-ylmethylsulfanyl)-propionamide was dissolved in CH3OH (10 mL) and an aqueous solution of Oxone® (3 g in 10 mL H2O, 10 mmol) was added. The reaction mixture was stirred at room temperature 3 h. Solvent was removed under the reduced pressure. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine and dried with MgSO4. The solvent was removed under the reduced pressure and the crude product was purified by prep-HPLC to isolate the title compound from the diastereomeric mixture.

Workup

  1. customSolvent was removed under the reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed under the reduced pressure
  6. customthe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-bb69a977a3414a49bd3a936562250b56
Source dataset
uspto-grants-2011_02
Patent number
US07893093B2

Reaction notes

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