Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 → Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988233Notes

Reaction equation

HRID 1988233 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([N:13]([CH3:38])[C@H:14]([C:18]([N:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[H][H]>CO.[Pd]>[NH2:1][C@H:2]([C:11]([N:13]([CH3:38])[C@H:14]([C:18]([N:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH:24]=1)=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 131727502Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 57729175Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.73 g, 2.61 mmol) and 10% palladium/carbon (340 mg) in methanol (50 ml) was stirred at room temperature in a hydrogen atmosphere for 17 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: chloroform:methanol:aqueous ammonia=100:10:1) to give Phe(4-F)-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (1.25 g, 91%). EI-MS:528 (M+)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55c78b3d148e4d9d89ff7e18f9873d97
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

Loading…