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

HRID 644450

Reaction equation

HRID 644450 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([O:16][C:17]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=1[C:19]([OH:21])=O)(=[O:15])[CH3:14].[NH2:27][C@@H:28]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:29]([NH:31][C:32]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=1)=[O:30].ON1C2C=CC=CC=2N=N1.Cl>CN(C)C=O>[C:13]([O:16][C:17]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:18]=1[C:19]([NH:27][C@H:28]([C:29](=[O:30])[NH:31][C:32]1[CH:37]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:35]=[C:34]([C:42]([F:43])([F:44])[F:45])[CH:33]=1)[CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:21])(=[O:15])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28208132-(Acetyloxy)-5-chlorobenzoic acidHCID 57459262(S)-2-Amino-3-phenyl-N-[3,5-bis(trifluoromethyl)phenyl]propionamide

Product 1

HCID 86602737(S)-2-Acetoxy-5-chloro-N-(2-phenyl-1-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-ethyl)benzamideYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC.HCl (184 mg, 0.96 mmol) was added to a solution of 2-acetoxy-5-chlorobenzoic acid (104 mg, 0.48 mmol), (S)-2-amino-3-phenyl-N-[3,5-bis(trifluoromethyl)phenyl]propionamide (0.20 g, 0.48 mmol) and 1-hydroxybenzotriazole (71.4 mg, 0.53 mmol) in N,N-dimethylformamide (4 mL), and the mixture was stirred at room temperature for 3 hours. 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 purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1) to give the title compound (141.4 mg, 51.4%) as a white crystal.

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 purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-3180f86f225a4c408fb870677aa00fa7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Linked notes

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