Piperidine → {(S)-1-[(S)-2-((2S,4S)-4-Amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 1481923Notes

Reaction equation

HRID 1481923 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]3[CH2:22][C@@H:21]([C:23](=[O:32])[NH:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]([C:33](=[O:55])[C@@H:34]([NH:41][C:42](=[O:54])[C@@H:43]([N:45]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH3:46])[CH3:44])[CH:35]4[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:19]3)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CN(C=O)C>[C:50]([O:49][C:47](=[O:48])[N:45]([C@H:43]([C:42](=[O:54])[NH:41][C@@H:34]([CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C:33]([N:20]1[CH2:19][C@@H:18]([NH2:17])[CH2:22][C@H:21]1[C:23](=[O:32])[NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:55])[CH3:44])[CH3:46])([CH3:51])([CH3:52])[CH3:53]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 118677385((3S,5S)-5-benzylcarbamoyl-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-pyrrolidin-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 90231684{(S)-1-[(S)-2-((2S,4S)-4-Amino-2-benzylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl esterYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

((3S,5S)-5-Benzylcarbamoyl-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-pyrrolidin-3-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester (100 mg, 0.13 mmol) was dissolved in DMF (0.9 mL) at room temperature and piperidine (0.1 mL) was added. The mixture was stirred at room temperature for 30 minutes, concentrated and the residue purified by silica gel chromatography to give the title compound as a white foam (71 mg, 52%).

Workup

  1. concentrationconcentrated
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-3899d05e178347c980819fa3ccfea9da
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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