Glycine, N-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl]-D-alanyl]-, phenylmethyl ester → HCID 71355766, compound

HRID 652376Notes

Reaction equation

HRID 652376 reaction equation
[NH:1]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@H:2]([C:10]([NH:12][C@@H:13]([C:15]([NH:17][CH2:18][C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:16])[CH3:14])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.[Pd]>[NH:1]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[C@H:2]([C:10]([NH:12][C@@H:13]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH3:14])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 14330670Glycine, N-[N-[N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl]-D-alanyl]-, phenylmethyl ester

Product 1

HCID 71355766HCID 71355766, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Boc-Phe-D-Ala-Gly-OBzl (2.4 g, 4.96 mmole) was dissolved in MeOH (50 ml), and H2 gas was passed through the solution in the presence of Pd-C for 4 hours. Pd-C was removed by filtration, and MeOH was distilled off. To the thus-obtained residue MeOH/Et2O and N-hexane were added. The thus-precipiated powder was separated by filtration and reprecipitated with AcOEt/n-hexane to obtain the desired product (1.95 g, 100%). (4) Synthesis of Z-Cys(4-CH3Bzl)-Phe-D-Ala-Gly-OH

Workup

  1. customPd-C was removed by filtration, and MeOH
  2. distillationwas distilled off
  3. additionTo the thus-obtained residue MeOH/Et2O and N-hexane were added
  4. customThe thus-precipiated powder was separated by filtration
  5. customreprecipitated with AcOEt/n-hexane

Sources & evidence

ORD record
ord-ab01e6da3cad4f41b397d73fd6e9f212
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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