Water → HCID 11525929, compound

HRID 1696064Notes

Reaction equation

HRID 1696064 reaction equation
[C:1]([C:3]1([NH:6][C:7](=[O:31])[C@@H:8]([NH:18][C@@H:19]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:20]([F:23])([F:22])[F:21])[CH2:9][S:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4]1)#[N:2].[OH:32]OS([O-])=O.[K+].[OH2:38]>CO>[C:1]([C:3]1([NH:6][C:7](=[O:31])[C@@H:8]([NH:18][C@@H:19]([C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[C:20]([F:22])([F:23])[F:21])[CH2:9][S:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)(=[O:32])=[O:38])[CH2:4][CH2:5]1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 66972513HCID 66972513, compound

Product 1

HCID 11525929HCID 11525929, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-cyanocyclopropyl)-2(R)-[2,2,2-trifluoro-1(S)-(4-fluorophenyl)ethylamino]-3-(pyridin-3-ylmethylsulfanyl)propionamide was dissolved in MeOH (3 ml) and OXONE® (460 mg, 1.5 mmol) in H2O (3 ml) was added. After stirring at rt for 2 h, the solvent was removed and the residue was extracted with ethyl acetate. The organic layer was dried with MgSO4 and the solvent was removed under reduced pressure. The title compound was separated by Prep-HPLC.

Workup

  1. customthe solvent was removed
  2. extractionthe residue was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried with MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customThe title compound was separated by Prep-HPLC

Sources & evidence

ORD record
ord-5deeeb4b144b49c6b966c45100c3d2ac
Source dataset
uspto-grants-2012_04
Patent number
US08163735B2

Reaction notes

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