3-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester → Boc-Phe-betaAla-OH

HRID 467355Notes

Reaction equation

HRID 467355 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]CC1C=CC=CC=1)=[O:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.[Pd]>[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 136862023-[[(S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester

Product 1

HCID 14330680Boc-Phe-betaAla-OH

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.0 g Boc-Phe-βAla-OBzl was reduced in 50 ml MeOH in the presence of Pd-black as a catalyst, and this was followed by concentration; the resulting residue was dissolved in 30 ml AcOEt, after which it was crystallized with 0.80 ml CHA and collected by filtration.

Workup

  1. concentrationthis was followed by concentration
  2. dissolutionthe resulting residue was dissolved in 30 ml AcOEt
  3. customafter which it was crystallized with 0.80 ml CHA
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d9e70b58f34e47899769f70bb4eb5d14
Source dataset
uspto-grants-1992_10
Patent number
US05159061

Reaction notes

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