Ethyl Acetate → N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester

HRID 1590115Notes

Reaction equation

HRID 1590115 reaction equation
Br.Br.[CH3:3][O:4][C:5](=[O:25])[C@H:6]([CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)[NH:7][C:8](=[O:18])[C@H:9]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:10].C1(=O)N([O:31][C:32](=O)[C@H:33]([CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])C(=O)CC1.C(OCC)(=O)C>CN(C)C=O.C(N(CC)CC)C>[CH3:3][O:4][C:5](=[O:25])[C@H:6]([CH2:19][C:20]1[N:24]=[CH:23][NH:22][CH:21]=1)[NH:7][C:8](=[O:18])[C@H:9]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:10][C:32](=[O:31])[C@H:33]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 107447tert-Butyl (S)-(1-benzyl-2-((2,5-dioxo-1-pyrrolidinyl)oxy)-2-oxoethyl)carbamateHCID 178419261HCID 178419261, compound

Product 1

HCID 178501419N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl esterYield 72.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

L-Phenylalanyl-L-histidine methyl ester dihydrobromide(1.75 g) is dissolved in a mixture of dimethylformamide (10 ml) and triethylamine(1.4 ml), and N-tert-butoxycarbonyl-L-phenylalanine succinimido ester (1.34 g) is added thereto. The mixture is stirred at room temperature overnight. Ethyl acetate is added to the mixture, and insoluble materials are filtered off. The filtrate is washed with an aqueous sodium bicarbonate solution, and an aqueous sodium chloride solution is added thereto. The precipitated crystals are washed with ethyl acetate and water and then dried to give N-tert-butoxycarbonyl-L-phenylalanyl-L-phenylalanyl-L-histidine methyl ester(1.5 g) as colorless crystals. Yield: 71.8%

Workup

  1. additionis added
  2. filtrationare filtered off
  3. washThe filtrate is washed with an aqueous sodium bicarbonate solution
  4. additionan aqueous sodium chloride solution is added
  5. washThe precipitated crystals are washed with ethyl acetate and water
  6. customdried

Sources & evidence

ORD record
ord-51fc25ae16d84677bb8aa91e5a6da399
Source dataset
uspto-grants-1993_04
Patent number
US05202312

Reaction notes

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