Trifluoroacetic acid → (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamide

HRID 394019Notes

Reaction equation

HRID 394019 reaction equation
C([O:5][C@H:6]1[CH2:10][N:9]([C:11](=[O:32])[CH2:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:8]([C:33]([N:35]2[CH2:39][CH2:38][CH2:37][C@@H:36]2[C:40]([NH:42][CH2:43][C@H:44]2[CH2:49][CH2:48][CH2:47][NH:46][CH2:45]2)=[O:41])=[O:34])[CH2:7]1)(C)(C)C.FC(F)(F)C(O)=O>>[OH:5][C@H:6]1[CH2:10][N:9]([C:11](=[O:32])[CH2:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:8]([C:33]([N:35]2[CH2:39][CH2:38][CH2:37][C@@H:36]2[C:40]([NH:42][CH2:43][C@H:44]2[CH2:49][CH2:48][CH2:47][NH:46][CH2:45]2)=[O:41])=[O:34])[CH2:7]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12149959(2R)-1-{(2S,4R)-4-tert-butoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamide

Product 1

HCID 12149960(2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamideYield 103.3%

Procedure

To 1.65 g of (2R)-1-{(2S,4R)-4-tert-butoxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonyl-N-((3S)-3-piperidylmethyl)pyrrolidine-2-carboxamide, 5 ml of trifluoroacetic acid was added at room temperature, followed by 1 hour's stirring at the same temperature. The reaction liquid was distilled off under reduced pressure, diluted with chloroform, rendered basic with 4N aqueous sodium hydroxide solution, extracted with chloroform and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, 1.56 g of the title compound was obtained as a white foamy substance.

Workup

  1. customThe reaction liquid
  2. distillationwas distilled off under reduced pressure
  3. additiondiluted with chloroform
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-ae1f1e57015d4bb5a02ece64af0529a2
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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