Boc-D-Trp(CH2CO2Et)-OBzl → Boc-D-Trp(CH2CO2Et)-OH

HRID 2082214Notes

Reaction equation

HRID 2082214 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:2]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1>C(O)C.[Pd]>[NH:1]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C@@H:2]([C:19]([OH:21])=[O:20])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=1

Participants

4

Reactant 1

HCID 131717763Boc-D-Trp(CH2CO2Et)-OBzl

Product 1

HCID 131717764Boc-D-Trp(CH2CO2Et)-OHYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of Boc-D-Trp(CH2CO2Et)-OBzl (4.14 g) in ethanol (60 ml) was added 5% palladium on carbon (0.7 g) and the mixture was hydrogenated for one and half an hour under atmospheric pressure. Filtration of the catalyst and concentration of the filtrate under vacuum gave Boc-D-Trp(CH2CO2Et)-OH as an amorphous solid (3.06 g).

Workup

  1. customwas hydrogenated for one and half an hour under atmospheric pressure
  2. filtrationFiltration of the catalyst and concentration of the filtrate under vacuum

Sources & evidence

ORD record
ord-fd6a5b44456442b6b07a2549bc29ec31
Source dataset
uspto-grants-1993_02
Patent number
US05187156

Reaction notes

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