Trifluoroacetic acid → 2-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acid

HRID 446017Notes

Reaction equation

HRID 446017 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[CH2:19][N:20]1[CH2:24][C@@H:23]([CH3:25])[C@@:22]([CH2:42][C:43]([O:45]C(C)(C)C)=[O:44])([C:26](=[O:41])[NH:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=3)[CH2:30][CH2:29]2)[CH2:21]1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[C:10]=1[CH2:19][N:20]1[CH2:24][C@@H:23]([CH3:25])[C@@:22]([CH2:42][C:43]([OH:45])=[O:44])([C:26](=[O:41])[NH:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:34][C:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]=3)[CH2:30][CH2:29]2)[CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293811tert-Butyl 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetate

Product 1

HCID 712936432-[(3R*,4S*)-1-{[2-Chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acidYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 ml, 20.3 mmol) was added to a solution of tert-butyl 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetate obtained in Example 4i (353 mg, 0.577 mmol) in dichloromethane (400 μl), which was stirred at mom temperature for two hours. The reaction mixture was concentrated under reduced pressure and purified by ODS column chromatography (elution solvent: methanol/water) to give the title compound (215 mg, yield 67%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by ODS column chromatography (elution solvent: methanol/water)

Sources & evidence

ORD record
ord-94461e98f0084997baa80e4aff7eee8f
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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