تفاعل #4465

ord-b8a5aa9b39d74e0b898f76e9233cf62f

معادلة التفاعل

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester
CCOC(=O)/C=C/C(=O)c1ccccc1
E-ethyl-3-benzoyl-acrylate
→
CCOC(=O)[C@H](CC(=O)c1ccccc1)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
Nα -[1(S)-ethoxycarbonyl-3-phenyl-3-oxo-propyl]-Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester

المتفاعلات

CCOC(C)=O
ethyl acetate
CC(C)(C)OC(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)OC(C)(C)C
Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester
CCOC(=O)/C=C/C(=O)c1ccccc1
E-ethyl-3-benzoyl-acrylate

الكواشف

لا شيء

المذيبات

CCOCC
ether
CCOCC
diethyl ether

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىAfter evaporation of the solvent the title product
  2. 2
    أخرىis isolated on a Kieselgel column in the form of transparent oil

الإجراء التجريبي

8.0 g (20 mmoles) of Nε -t-butoxycarbonyl-(S)-lysyl-(S)-proline-t-butylester are dissolved in 100 ml of diethyl ether and 4.48 g (22 mmoles) of E-ethyl-3-benzoyl-acrylate are added to the solution. The reaction mixture is stirred at room temperature for 5 hours. After evaporation of the solvent the title product is isolated on a Kieselgel column in the form of transparent oil. Rf =0.49 i(in a 7:3 eluent mixture of ethyl acetate and ether).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04725617uspto-grants-1988_02