N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine benzyl ester → N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine

HRID 614204Notes

Reaction equation

HRID 614204 reaction equation
C([O:8][C:9](=[O:46])[C@H:10]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH:11][C:12](=[O:38])[CH2:13][NH:14][C:15](=[O:37])[CH2:16][NH:17][C:18](=[O:36])[C@H:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])C1C=CC=CC=1.[H][H]>[Pd].CO>[C:24]([O:23][C:21]([NH:20][C@H:19]([C:18]([NH:17][CH2:16][C:15]([NH:14][CH2:13][C:12]([NH:11][C@H:10]([C:9]([OH:46])=[O:8])[CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:38])=[O:37])=[O:36])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 15689706N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 15689707N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.6 parts N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine benzyl ester in 160 parts methanol is added 0.4 part palladium black metal catalyst. The resulting mixture is shaken with hydrogen at room temperature at atmospheric pressure for about 5 hours. The catalyst is then removed by filtration, and the solvent removed by evaporation under reduced pressure. The resulting crude material is purified using low-pressure chromatography to afford N-t-butoxycarbonyl-L-tyrosylglycylglycyl-L-phenylalanine.

Workup

  1. customThe catalyst is then removed by filtration
  2. customthe solvent removed by evaporation under reduced pressure
  3. customThe resulting crude material is purified

Sources & evidence

ORD record
ord-2ff2f70d70a248f2a2d2831391226cbf
Source dataset
uspto-grants-1979_03
Patent number
US04144228

Reaction notes

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