HCID 19705563, compound → HCID 19705478, compound

HRID 727571Notes

Reaction equation

HRID 727571 reaction equation
C([O:8][NH:9][C:10](=[O:43])[CH:11]([CH2:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[OH:8][NH:9][C:10](=[O:43])[CH:11]([CH2:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25]

Participants

4

Reactant 1

HCID 19705563HCID 19705563, compound

Product 1

HCID 19705478HCID 19705478, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of N-benzyloxy-α-[[[(4-methoxyphenyl)sulfonyl]amino]methyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (218 mg, 0.359 mmol) in EtOH (7 mL) is treated with palladium hydroxide on carbon (55 mg) and placed under a H2 atmosphere via a balloon. After 6.5 hours, the mixture is filtered, rinsing the residual solids with MeOH and CHCl3. The filtrate is concentrated to give 182 mg of a white solid. The material is crystallized from hot EtOAc with a trace of MeOH, eventually diluting with hexane, to provide 136 mg of the title compound as a solid (mp 195°-196° C.):

Workup

  1. filtrationthe mixture is filtered
  2. washrinsing the residual solids with MeOH and CHCl3
  3. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-c43ea76cce18437eb9b86b3d90ef1d98
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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