Trifluoroacetic acid → (s)-n-{(s)-1-Cyclohexyl-2-oxo-2-[(s)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethyl}-2-methylamino-propionamide

HRID 222507Notes

Reaction equation

HRID 222507 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]([C:11](=[O:40])[NH:12][C@@H:13]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:14](=[O:33])[N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=1)[CH3:10])C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:34]1([C@H:13]([NH:12][C:11](=[O:40])[C@@H:9]([NH:7][CH3:6])[CH3:10])[C:14](=[O:33])[N:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:21]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67003947((S)-1-{(S)-1-Cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 54669904(s)-n-{(s)-1-Cyclohexyl-2-oxo-2-[(s)-2-(3-phenoxy-phenyl)-pyrrolidin-1-yl]-ethyl}-2-methylamino-propionamideYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((S) 1-{(S)-1-cyclohexyl-2-oxo-2-[(S)-2-(3-phenoxy-phenyl)-pyrrolodin-1-yl]-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester (450 mgs, 0.79 mmol) in CH2Cl2 (20 mL) is added TFA (10 mL) and stirred for 30 minutes. The mixture is concentrated under reduced pressures and purified by reverse phase column chromatography to give the product as a TFA salt (370 mgs, 82%). LCMS m/z 464.1 (M+1).

Workup

  1. concentrationThe mixture is concentrated under reduced pressures
  2. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-7597882d5338495e94060dcb1eca96e1
Source dataset
uspto-grants-2012_06
Patent number
US08207183B2

Reaction notes

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