HCID 11398881, compound → HCID 57720719, compound

HRID 1985809Notes

Reaction equation

HRID 1985809 reaction equation
[C:1]([C:3]1([NH:9][C:10](=[O:37])[C@@H:11]([NH:24][C@@H:25]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:26]([F:29])([F:28])[F:27])[CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]S[CH2:5][CH2:4]1)#[N:2].OO[S:40]([O-:42])=[O:41].[K+]>CO>[C:1]([C:3]1([NH:9][C:10](=[O:37])[C@@H:11]([NH:24][C@@H:25]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:26]([F:29])([F:27])[F:28])[CH2:12][S:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)(=[O:15])=[O:14])[CH2:4][CH2:5][S:40](=[O:42])(=[O:41])[CH2:7][CH2:8]1)#[N:2]

Participants

4

Reactant 2

HCID 11398881HCID 11398881, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 57720719HCID 57720719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

N-(4-cyanotetrahydrothiopyran-4-yl)-3-(4-fluorophenylmethanesulfonyl)-2(R)-(2,2,2-trifluoro-1(S)-4-fluorophenylethylamino)propionamide (24 mg) was weighed into a 25 mL pear flask fitted with a stir bar and vented cap. Methanol (4.75 mL) was added and the reaction mixture was stirred at 50° C. to obtain a clear colorless solution. OXONE® (0.43 mL of a 0.30M aqueous solution) was added. A white precipitate formed. After 2 h, methanol was removed on a rotary evaporator and the residue was partitioned between 10 mL water and 10 mL dichloromethane. The organic phase was separated, washed with water and brine and dried over anhydrous MgSO4 and concentrated to give the title compound (16 mg) as a white solid.

Workup

  1. customfitted with a stir bar
  2. customto obtain a clear colorless solution
  3. customA white precipitate formed
  4. custommethanol was removed on a rotary evaporator
  5. customthe residue was partitioned between 10 mL water and 10 mL dichloromethane
  6. customThe organic phase was separated
  7. washwashed with water and brine
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d048983fb6624be083e2b54b762e33a4
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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