(2S,4S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester → (2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid

HRID 1481921Notes

Reaction equation

HRID 1481921 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][N:12]1[C:34](=[O:56])[C@@H:35]([NH:42][C:43](=[O:55])[C@@H:44]([N:46]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH3:47])[CH3:45])[CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)=[O:10])C1C=CC=CC=1>CO.[Pd]>[C:51]([O:50][C:48]([N:46]([CH3:47])[C@@H:44]([CH3:45])[C:43]([NH:42][C@@H:35]([CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[C:34]([N:12]1[CH2:13][C@@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:15][C@H:11]1[C:9]([OH:10])=[O:8])=[O:56])=[O:55])=[O:49])([CH3:54])([CH3:53])[CH3:52]

Participants

4

Reactant 1

HCID 90220266(2S,4S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 90231415(2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acidYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester (1.2 g, 1.56 mmol) was dissolved in methanol (15 mL) and 10% Pd—C (200 mg) was added. The mixture was stirred under hydrogen (1 atm) for 1 h, filtered through Celite and concentrated to give the title compound (800 mg, 76%) as a colorless oil which solidified upon standing and was used without purification.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c0446cfb9cbd47e087bac2a174b1ecb1
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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