Methanol → Boc-Phe-Gly-OH

HRID 652379Notes

Reaction equation

HRID 652379 reaction equation
[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CO>[Pd].CC(O)=O>[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:2]([C:10]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 15601613HCID 15601613, compound

Product 1

HCID 7014899Boc-Phe-Gly-OHYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Boc-Phe-Gly-OBzl (6.2 g, 15 mmole) was suspended in the mixtured solvent of MeOH (80 ml) and AcOH (30 ml), and then H2 gas was passed through the solution in the presence of Pd-C for 4 hours. Pd-C was removed by filtration, and the solvent was distilled off. The thus-obtained residue was recrystalized two times with AcOEt/n-hexane to obtain the object product (4.49 g, 92.8%).

Workup

  1. customPd-C was removed by filtration
  2. distillationthe solvent was distilled off
  3. customThe thus-obtained residue was recrystalized two times with AcOEt/n-hexane

Sources & evidence

ORD record
ord-775688068557490fb481461376de20d4
Source dataset
uspto-grants-1987_06
Patent number
US04670540

Reaction notes

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