Реакция #541614

ord-117b97f8e8ef46afb195efb6b8e752ec

Уравнение реакции

CCOC(=O)C1CC2(CCN(C(=O)OC(C)(C)C)CC2)CN1
8-(1,1-dimethylethyl) 3-ethyl 2,8-diazaspiro[4.5]decane-3,8-dicarboxylate
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
COC(=O)N[C@H](C(=O)O)C(C)C
N-[(methyloxy)carbonyl]-L-valine
CCN(C(C)C)C(C)C
Hunig's base
CCOC(=O)C1CC2(CCN(C(=O)OC(C)(C)C)CC2)CN1C(=O)[C@@H](NC(=O)OC)C(C)C
title compound
Выход 55.5%
CCOC(=O)C1CC2(CCN(C(=O)OC(C)(C)C)CC2)CN1C(=O)[C@@H](NC(=O)OC)C(C)C
8-(1,1-dimethylethyl) 3-ethyl 2-{N-[(methyloxy)carbonyl]-L-valyl}-2,8-diazaspiro[4.5]decane-3,8-dicarboxylate
Выход 55.5%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe reaction was concentrated in vacuo
  2. 2
    Другоеpurified by silica gel chromatography
  3. 3
    Промывкаeluting with 15-80% hexanes/EtOAc

Методика

To a solution of 8-(1,1-dimethylethyl) 3-ethyl 2,8-diazaspiro[4.5]decane-3,8-dicarboxylate (131) (150 mg, 0.48 mmol), HATU (183 mg, 0.48 mmol) and N-[(methyloxy)carbonyl]-L-valine (93 mg, 0.53 mmol) in anhydrous CH2Cl2 (4 mL) was added Hunig's base (0.17 mL, 0.96 mmol) and the reaction stirred at room temperature under nitrogen for 2 h. The reaction was concentrated in vacuo and purified by silica gel chromatography eluting with 15-80% hexanes/EtOAc to afford the title compound as a pale yellow oil (125 mg, 55% yield).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08492554B2uspto-grants-2013_07