Triethylamine → Z-Pro-ONp

HRID 1283777Notes

Reaction equation

HRID 1283777 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:26]([C:29]1[CH:34]=[CH:33][C:32](OC(ON=C(C#N)C(OCC)=O)=O)=[CH:31][CH:30]=1)([O-:28])=[O:27]>C(OCC)(=O)C>[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([O:14][C:13](=[O:15])[C@@H:12]2[CH2:16][CH2:17][CH2:18][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])=[CH:31][CH:30]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 54332477Ethyl 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetate

Product 1

HCID 10133728Z-Pro-ONpYield 53.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-proline (1.25 g) and triethylamine (0.70 ml) in ethyl acetate (15 ml), ethyl 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetate (1.55 g) in powder form is added at room temperature while stirring. The resulting mixture is stirred for 4 hours and then extracted with ethyl acetate. The extract is washed with water, dried and concentrated. The residue is recrystallized from an ethanol-petroleum ether mixture to give N-benzyloxycarbonyl-L-proline p-nitrophenyl ester (1.0 g). M.P. 94° - 96°C.

Workup

  1. stirringThe resulting mixture is stirred for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is recrystallized from an ethanol-petroleum ether mixture

Sources & evidence

ORD record
ord-9cdc4526ac304d97a656c4b3cc9caa22
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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