2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide → 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-glycinyl-4-methylvalerohydrazide

HRID 651805Notes

Reaction equation

HRID 651805 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:19]([NH:21][NH:22][C:23](=[O:36])[CH2:24][NH:25]C(OCC1C=CC=CC=1)=O)=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:19]([NH:21][NH:22][C:23](=[O:36])[CH2:24][NH2:25])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 702395472(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide

Product 1

HCID 867573112(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-glycinyl-4-methylvalerohydrazideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.95 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2′-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide in 30 ml of methanol was hydrogenated in the presence of 0.300 g of 5% palladium-on-carbon for 0.5 hours. The mixture was filtered and evaporated to give 2.2 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2′-glycinyl-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated

Sources & evidence

ORD record
ord-de776090e824496c884bd04b95d6a22f
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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