Ethylmorpholine → Z-Phe-ONp

HRID 1283776Notes

Reaction equation

HRID 1283776 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(N1CCOCC1)C.[N+:31]([C:34]1[CH:39]=[CH:38][C:37](OC(ON=C(C#N)C(OCC)=O)=O)=[CH:36][CH:35]=1)([O-:33])=[O:32]>C(Cl)Cl>[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([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:36][CH:35]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 7525EthylmorpholineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 54332477Ethyl 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetate

Product 1

HCID 151025Z-Phe-ONpYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of N-benzyloxycarbonyl-L-phenylalanine (1.5 g) and 4-ethylmorpholine (0.63 ml) in dry methylene chloride (20 ml), ethyl 2-p-nitrophenyloxycarbonyloxyimino-2-cyanoacetate (1.55 g) is added at room temperature while stirring. The resulting mixture is stirred for 3 hours and extracted with ethyl acetate. The extract is washed with water, dried and concentrated. The residue is triturated with ethanol, and the obtained powder is collected by filtration and dried to give N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester (1.0 g). M.P. 124° - 126°C.

Workup

  1. stirringThe resulting mixture is stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is triturated with ethanol
  7. filtrationthe obtained powder is collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-6389fe13e9fe4a51ade61a085edae354
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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