Реакция #70369

ord-04d4f36299c147a0ba6723e5763ed264

Уравнение реакции

C[C@]12CCC(=O)CC1[C@@H](C(=O)O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-carboxyandrostane-3,17-dione
CO
MeOH
CCN=C=NCCCN(C)C
EDAC
O
H2O
→
COC(=O)[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
title compound
COC(=O)[C@H]1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6α-Methoxycarbonylandrostane-3,17-dione

Реактанты

C[C@]12CCC(=O)CC1[C@@H](C(=O)O)C[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
6α-carboxyandrostane-3,17-dione
CO
MeOH
CCN=C=NCCCN(C)C
EDAC
O
H2O

Реагенты

CN(C)c1ccncc1
DMAP

Растворители

ClCCl
CH2Cl2

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Экстракцияthe mixture was extracted with CH2Cl2 (2×)
  2. 2
    ПромывкаThe combined organic extracts were washed with H2O, brine
  3. 3
    Сушкаdried over Na2SO4
  4. 4
    Фильтрацияfiltered
  5. 5
    Другоеevaporated to dryness
  6. 6
    ДругоеThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40)

Методика

To a stirred solution of 6α-carboxyandrostane-3,17-dione (Prepn. 16, 680 mg) in CH2Cl2 (30 mL) at 0° C., MeOH (160 μL), DMAP (20 mg) and EDAC (800 mg) were added. After stirring overnight at room temperature, H2O was added and the mixture was extracted with CH2Cl2 (2×). The combined organic extracts were washed with H2O, brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 60/40) to give the title compound II-ag (500 mg, 70%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.59 (3H, s), 2.53-0.75 (21H, m), 1.02 (3H, s), 0.79 (3H, s).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08536160B2uspto-grants-2013_09