Hydrochloric Acid → (S)-5-Chloro-2-hydroxy-N-(2-phenyl-1-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl)-ethyl)benzamide

HRID 644451Notes

Reaction equation

HRID 644451 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][C:8]=1[C:9]([NH:11][C@H:12]([C:20](=[O:36])[NH:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])(=O)C.Cl>CO.O1CCCC1>[Cl:41][C:38]1[CH:39]=[CH:40][C:7]([OH:6])=[C:8]([CH:37]=1)[C:9]([NH:11][C@H:12]([C:20](=[O:36])[NH:21][C:22]1[CH:27]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:25]=[C:24]([C:32]([F:33])([F:34])[F:35])[CH:23]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602737(S)-2-Acetoxy-5-chloro-N-(2-phenyl-1-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-ethyl)benzamide

Product 1

HCID 10256472(S)-5-Chloro-2-hydroxy-N-(2-phenyl-1-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl)-ethyl)benzamideYield 56.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

5N Aqueous sodium hydroxide (0.2 mL) was added to a solution of (S)-2-acetoxy-5-chloro-N-(2-phenyl-1-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-ethyl)benzamide (141.4 mg, 0.25 mmol) in a mixed solvent of methanol/tetrahydrofuran (2 mL+2 mL), and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. After the ethyl acetate layer was washed successively with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation of the solvent under reduced pressure was crystallized by ethyl acetate/isopropyl ether/n-hexane to give the title compound (74.4 mg, 56.8%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the ethyl acetate layer was washed successively with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas crystallized by ethyl acetate/isopropyl ether/n-hexane

Sources & evidence

ORD record
ord-22f074228d2646728cc185c9a793320c
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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