chloroform methanol HOAc → Nalpha-Acetyl-p-Amino-L-Phenylalanyl-Glycine Benzyl Ester

HRID 280044Notes

Reaction equation

HRID 280044 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[CH2:10][NH:11][C:12](=[O:28])[C@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)[NH:14][C:15](=[O:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO.C(O)(=O)C>CO.[Pt](=O)=O>[CH2:1]([O:8][C:9](=[O:29])[CH2:10][NH:11][C:12](=[O:28])[C@H:13]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[NH:14][C:15](=[O:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 21866353chloroform methanol HOAcHCID 53962211Nalpha-Acetyl-p-Nitro-L-Phenylalanyl-Glycine Benzyl Ester

Product 1

HCID 54160731Nalpha-Acetyl-p-Amino-L-Phenylalanyl-Glycine Benzyl Ester

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Compound 14 (267 mg, 0.67 mmol) was dissolved in methanol (50 ml). Platinum dioxide (3% of weight of peptide) was added, and the mixture was hydrogenated at atmospheric pressure. After 4 hours TLC (chloroform/methanol/acetic acid: 85/10/5) showed a clean conversion to the amine. The catalyst was separated by decantation, and the solvent was removed under reduced pressure. Compound 15 was obtained in nearly quantitative yield as a glassy solid.

Workup

  1. customThe catalyst was separated by decantation
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fa13dea7a2884060b3dfb881104c1f5b
Source dataset
uspto-grants-1986_05
Patent number
US04587046

Reaction notes

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