Trifluoroacetic acid → Ammonia

HRID 380511Notes

Reaction equation

HRID 380511 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([N:19]2[CH2:23][C@@H:22]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C@H:21]([CH2:29][N:30]3[CH2:35][CH2:34][CH:33]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)[CH2:20]2)=[O:18])[CH:10]=[C:9]1C)=O)(C)(C)C.[C:44]([C:48]([OH:50])=[O:49])(F)(F)F>O>[NH3:8].[C:48]([CH2:44][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([N:19]2[CH2:23][C@@H:22]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C@H:21]([CH2:29][N:30]3[CH2:35][CH2:34][CH:33]([C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)[CH2:32][CH2:31]3)[CH2:20]2)=[O:18])[CH:10]=[CH:9]1)([OH:50])=[O:49]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757489HCID 86757489, compound

Product 2

HCID 222AmmoniaHCID 20694257HCID 20694257, compound

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A solution of 0.185 g (0.307 mmol) of 1-(1-t-butoxycarbonyl methyl-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(R)-(3-thienyl)pyrrolidine in 6 mL of CF3CO2H and 5 drops of H2O was stirred at rt for 1.5 h. The reaction mixture was concentrated and purified by chromatography (silica, CH2Cl2: ethyl acetate: NH3 (2M in MeOH), 10:10:1, then CH2Cl2: MeOH: NH3 (2M in MeOH) 100:8:4) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography (silica, CH2Cl2

Sources & evidence

ORD record
ord-9789af4c8373461bbd4c4f5d74d433fd
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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