(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane → 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

HRID 54074

Reaction equation

HRID 54074 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:13]1[O:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([NH:27][C:28]([CH:30]1[NH:34][CH:33]2[CH2:35][CH2:36][CH2:37][CH:32]2[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:13]([OH:15])[CH2:14][N:34]1[CH:30]([C:28]([NH:27][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:29])[CH2:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH:33]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutaneHCID 19031947N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide

Product 1

HCID 572861401-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.98 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane and 2.1 g of N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide in 50 ml of ethanol was heated at reflux for 10 hours and the solvent was then removed by evaporation. Chromatography on silica gel using System H for the elution then gave 4.7 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-octahydro-cyclopenta[b]pyrrole-2-carboxamide as a mixture of four diastereomers: MS: m/e 508 [M+H]+.

Workup

  1. temperatureat reflux for 10 hours
  2. customthe solvent was then removed by evaporation
  3. washChromatography on silica gel using System H for the elution

Sources & evidence

ORD record
ord-7ff4e79b9bb74f40af70585bb8a7bf69
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Linked notes

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