Water → Z-Phe-ONp

HRID 1283775Notes

Reaction equation

HRID 1283775 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:30]([C:33]1[CH:38]=[CH:37][C:36](OC(ON=C(C#N)C(N)=O)=O)=[CH:35][CH:34]=1)([O-:32])=[O:31].O>O1CCCC1>[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([O:21][C:20](=[O:22])[C@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])=[CH:35][CH:34]=1)([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 543599642-p-Nitrophenyloxycarbonyloxyimino-2-cyanoacetic acid amide

Product 1

HCID 151025Z-Phe-ONpYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-phenyl alanine (0.6 g) and triethylamine (0.28 ml) in dry tetrahydrofuran (12 ml), 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetic acid amide (0.6 g) is added, and the resulting mixture is stirred at room temperature for 1.5 hours. The reaction mixture is admixed with water and extracted with ethyl acetate. The organic layer is washed with an aqueous solution of sodium chloride, dried and concentrated. The residue is recrystallized from an ethanol-petroleum ether mixture to give N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (0.5 g) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with an aqueous solution of sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is recrystallized from an ethanol-petroleum ether mixture

Sources & evidence

ORD record
ord-a8a5f0dd095d4edda4bdcca9c0cc71d2
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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