Ethyl Acetate → N-[2-Amino-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2301025Notes

Reaction equation

HRID 2301025 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:28])[C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])([O-])=O.C([O-])=O.[NH4+].C(OCC)(=O)C>CO.[Pd].O>[NH2:1][C:4]1[CH:9]=[C:8]([S:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:12])[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:28])[C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:23])[F:24]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 106219143,3,3-Trifluoro-2-hydroxy-2-methyl-N-[2-nitro-4-(phenylsulfonyl)phenyl]propanamide

Product 1

HCID 22287234N-[2-Amino-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideYield 96%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of N-[2-nitro-4-(phenylsulphonyl)phenyl]2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (J. Med. Chem., 1996, 39, 4592) (0.293 g) in methanol (5 ml) was added to a stirred suspension of 10% palladium on carbon (0.03 g) in methanol (2 ml) under an atmosphere of argon. A solution of ammonium formate (0.176 g) in water (2 ml) was added and the mixture was heated under reflux for 2 hours then cooled. Ethyl acetate (20 ml) was added and the mixture was filtered through diatomaceous earth. The filter was washed with ethyl acetate (2×10 ml) and the filtrates were combined, washed with water and brine then dried. Volatile material was removed by evaporation to give the title compound (0.261 g) as a solid. NMR: 1.55 (s, 3H), 5.3 (s, 2H), 7.1 (dd, 1H), 7.3 (d, 1H), 7.4 (m, 2H), 7.5-7.7 (m, 3H), 7.85 (d, 2H), 9.6 (s, 1H); MS (ESP−): 387.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethen cooled
  4. filtrationthe mixture was filtered through diatomaceous earth
  5. washThe filter was washed with ethyl acetate (2×10 ml)
  6. washwashed with water and brine
  7. customthen dried
  8. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-dc3e44f9d19844edae36daec423df60f
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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