Water → N-[2-Acetamido-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2301026Notes

Reaction equation

HRID 2301026 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[C:10]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:9]=[CH:8][C:7]=1[NH:21][C:22](=[O:30])[C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:26])[F:25].O>N1C=CC=CC=1>[C:1]([NH:5][C:6]1[CH:11]=[C:10]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:13])=[O:14])[CH:9]=[CH:8][C:7]=1[NH:21][C:22](=[O:30])[C:23]([OH:29])([CH3:28])[C:24]([F:27])([F:25])[F:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 22287234N-[2-Amino-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 22287178N-[2-Acetamido-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.018 ml) was added to an ice-cooled solution of N-[2-amino-4-(phenylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 184) (0.097 g) in pyridine (1 ml) and the solution was allowed to warm up to ambient temperature over 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 10-40% ethyl acetate/hexane to give the title compound (0.89 g) as a solid. Mp 205-207° C.; NMR: 1.5 (s, 3H), 2.1 (s, 3H), 7.57-7.75 (m, 4H), 7.8-7.9 (m, 2H), 7.9-8.05 (m, 3H), 9.8 (brs, 1H), 10.1 (brs, 1H); MS (ESP−): 429.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  6. washeluting with 10-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-99cc0a8b9b4442a39b4f925cdffd939d
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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