Water → (+/-)-1-[3-({Cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylic acid

HRID 1475683Notes

Reaction equation

HRID 1475683 reaction equation
[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([O:19]C(C)(C)C)=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68170307(+/-)-Tert-butyl 1-[3-({cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}-amino)benzyl]cyclopropanecarboxylate

Product 1

HCID 68006924(+/-)-1-[3-({Cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}amino)benzyl]cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.83 g (9.63 mmol) of (+/−)-tert-butyl 1-[3-({cyclopentyl[4-(trifluoromethyl)phenyl]acetyl}-amino)benzyl]cyclopropanecarboxylate were dissolved in 25 ml of dichloromethane and, after addition of a drop of water, 7.5 ml of TFA were added at RT. The reaction mixture was stirred at RT for 2 h and then concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1). This gave 3.89 g (90.8% of theory) of the target compound.

Workup

  1. additionwere added at RT
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→2:1)

Sources & evidence

ORD record
ord-52ac87549b9e4fec85fd35ac17f39377
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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