(3R*,4R*)-3-({Cyclopropyl-[2-(3-nitro-phenyl)-acetyl]-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester → HCID 68617160, compound

HRID 1158362Notes

Reaction equation

HRID 1158362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([CH:48]2[CH2:50][CH2:49]2)[C:36](=[O:47])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([N+:44]([O-])=O)[CH:39]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][N:35]([C:36](=[O:47])[CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([NH2:44])[CH:39]=2)[CH:48]2[CH2:49][CH2:50]2)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 68618278(3R*,4R*)-3-({Cyclopropyl-[2-(3-nitro-phenyl)-acetyl]-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68617160HCID 68617160, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

At RT H2 is passed through a suspension of (3R*,4R*)-3-({cyclopropyl-[2-(3-nitro-phenyl)-acetyl]-amino}-methyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (660 mg, 0.95 mmol) and Raney-Ni (100 mg) for several hours. After completion of the reaction the mixture is filtered over Celite and the solvent is evaporated to give the title compound which is used without further purification. MS (LC-MS): 667.0 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 5.33 min.

Workup

  1. customAfter completion of the reaction the mixture
  2. filtrationis filtered over Celite
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-ae16dedc2cf1457c95ba8f98acb37ae6
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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