Z-N-Me-Phg-Tyr(3-tBu)-NH2 → N-Me-Phg-Tyr(3-tBu)-NH2

HRID 1383720Notes

Reaction equation

HRID 1383720 reaction equation
[C:1]([N:11](C)[C@H:12]([C:19]([NH:21][C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=1)=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(OCC1C=CC=CC=1)=O.[H][H]>CO.[C].[Pd]>[NH:11]([CH3:1])[C@H:12]([C:19]([NH:21][C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:34])([CH3:32])[CH3:33])[CH:25]=1)=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH:11]([CH3:1])[C@@H:12]([C:19]([NH:21][C@H:22]([C:35]([NH2:37])=[O:36])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C:31]([CH3:34])([CH3:32])[CH3:33])[CH:25]=1)=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 131722734Z-N-Me-Phg-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 2

HCID 131722735N-Me-Phg-Tyr(3-tBu)-NH2HCID 131722736N-Me-D-Phg-Tyr(3-tBu)-NH2

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of Z-N-Me-Phg-Tyr(3-tBu)-NH2 (4.03 g) and 10% palladium carbon (2.0 g) in methanol (200 ml) was stirred in a hydrogen atmosphere for 4 hours. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of methylene chloride, methanol and aqueous ammonia at a ratio of 100:5:1) to give N-Me-Phg-Tyr(3-tBu)-NH2 in 1.48 g (50%) and N-Me-D-Phg-Tyr(3-tBu)-NH2 in the amount of 920 mg (31%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was distilled off under reduced pressure
  3. washeluting solvent

Sources & evidence

ORD record
ord-5e503fedd76b4d03ba186e1a75d7f57e
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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