Methylamine → 4-Fluoro-N-(3,3,3-trifluoro-2-hydroxy-1-methylcarbamoylpropyl)-2-trifluoromethylbenzamide

HRID 506490Notes

Reaction equation

HRID 506490 reaction equation
[F:1][C:2]([F:26])([F:25])[CH:3]([OH:24])[CH:4]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20])[C:5](OCC)=[O:6].[CH3:27][NH2:28]>C(O)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:10][CH:4]([C:5](=[O:6])[NH:28][CH3:27])[CH:3]([OH:24])[C:2]([F:26])([F:25])[F:1])=[O:23])=[C:13]([C:19]([F:22])([F:21])[F:20])[CH:14]=1

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 59432150Ethyl 4,4,4-trifluoro-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyrate

Product 1

HCID 594321624-Fluoro-N-(3,3,3-trifluoro-2-hydroxy-1-methylcarbamoylpropyl)-2-trifluoromethylbenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3.1 g (7.9 mmol) of ethyl 4,4,4-trifluoro-2-(4-fluoro-2-trifluoromethylbenzoylamino)-3-hydroxybutyrate were dissolved in ethanol. At RT, 20 ml of a 3.9% strength solution of methylamine in ethanol was added. After 5 h of stirring at RT, methylamine gas was introduced for 10 min and the mixture was stirred at RT for 16 h. The reaction solution was then concentrated, and the residue was washed with MTBE. This gave 1.8 g (61% of theory) of the title compound as colorless crystals (diastereomer ratio 3:1) of m.p. 212° C.

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. concentrationThe reaction solution was then concentrated
  3. washthe residue was washed with MTBE

Sources & evidence

ORD record
ord-7d1404678313473fb4d40962faac9285
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

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