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

HRID 445997Notes

Reaction equation

HRID 445997 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH2:12][N:13]1[CH2:17][C@@H:16]([CH3:18])[C@@:15]([CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])([C:19](=[O:33])[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]([F:32])[CH2:29][CH2:30][CH3:31])[CH2:23][CH2:22]2)[CH2:14]1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:9])[F:10])[C:3]=1[CH2:12][N:13]1[CH2:17][C@@H:16]([CH3:18])[C@@:15]([CH2:34][C:35]([OH:37])=[O:36])([C:19](=[O:33])[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]([F:32])[CH2:29][CH2:30][CH3:31])[CH2:23][CH2:22]2)[CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293836tert-butyl 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(2-fluoropentyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetate

Product 1

HCID 712936512-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(2-fluoropentyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the chiral form of tert-butyl 2-[(3R*,4S*)-1-{[2-chloro-6-(trifluoromethyl)phenyl]methyl}-3-{[1-(2-fluoropentyl)piperidin-4-yl]carbamoyl}-4-methylpyrrolidin-3-yl]acetate obtained in Example 1l (153 mg, 0.252 mmol), trifluoroacetic acid (2 ml, 26.9 mmol) and dichloromethane (dehydrated) (2 ml) was stirred at mom temperature for two hours and 35 minutes. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (ODS silica gel, elution solvent: water/methanol) to give the title compound (122 mg, yield 88%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (ODS silica gel, elution solvent: water/methanol)

Sources & evidence

ORD record
ord-a7527004dc5a4399ad077243593d151e
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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