Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 → (S)-N-((S)-1-amino-3-(3-tert-butyl-4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-amino-N-methyl-3-phenylpropanamido)-N,3-dimethylbutanamide

HRID 1383745Notes

Reaction equation

HRID 1383745 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([N:12]([CH3:37])[C@H:13]([C:17]([N:19]([CH3:36])[C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>CO.[C].[Pd]>[NH2:1][C@H:2]([C:10]([N:12]([CH3:37])[C@H:13]([C:17]([N:19]([CH3:36])[C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:30])([CH3:32])[CH3:31])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 131722753Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 44583348(S)-N-((S)-1-amino-3-(3-tert-butyl-4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-amino-N-methyl-3-phenylpropanamido)-N,3-dimethylbutanamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (610 mg) and 10% palladium carbon (100 mg) in methanol (15 ml) was stirred at room temperature in a hydrogen atmosphere for 17 hours. The reaction mixture was filtered and washed with methanol. The solvent was distilled off under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate) to yield Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 431 mg (89%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. distillationThe solvent was distilled off under reduced pressure
  4. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate)

Sources & evidence

ORD record
ord-f18124970cec4953a853d9e3d3d0dc9d
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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