반응 #683389

ord-66c92f9177d84b878df44fda7d3303ee

반응 방정식

CCOC(=O)C(=NOC(=O)OC(C)(C)C)C(=O)OCC
diethyl 2-tert-butoxycarbonyloxyiminomalonate
CC[C@H](C)[C@H](N)C(=O)O
L-isoleucine
[Na+].[OH-]
sodium hydroxide
CC[C@H](C)[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-tert-butoxycarbonyl-L-isoleucine
수율 103.7%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타tert-Butyl alcohol was removed from the reaction mixture under reduced pressure and water
  2. 2
    workup.ADDITIONwas added to the residue
  3. 3
    세척The mixture was washed with ether
  4. 4
    추출extracted with ethyl acetate
  5. 5
    세척The extract was washed with water
  6. 6
    기타dried
  7. 7
    농축concentrated

실험 절차

A solution of diethyl 2-tert-butoxycarbonyloxyiminomalonate (1.9 g.) in tert-butyl alcohol (5 ml.) was added to a solution of L-isoleucine (656 mg.) in a 1N sodium hydroxide aqueous solution (5.0 ml.), and the mixture was stirred for 3 hours at room temperature. tert-Butyl alcohol was removed from the reaction mixture under reduced pressure and water was added to the residue. The mixture was washed with ether, adjusted to pH 3 with a 5% citric acid aqueous solution and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give N-tert-butoxycarbonyl-L-isoleucine (1.2 g.), oil.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04010178uspto-grants-1977_03