Reaktion #1885026

ord-ce817106271445f88e2afb1b26de9ffa

Reaktionsgleichung

CC(C)C[C@H](NC(=O)CNC(=O)CNC(=O)OC(C)(C)C)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Boc-Gly-Gly-Leu Hydrocodone
Cl
HCl
→
CC(C)C[C@H](NC(=O)CNC(=O)CN)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
solid
Ausbeute 97.9%
CC(C)C[C@H](NC(=O)CNC(=O)CN)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Gly-Gly-Leu Hydrocodone
Ausbeute 97.9%

Edukte

CC(C)C[C@H](NC(=O)CNC(=O)CNC(=O)OC(C)(C)C)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Boc-Gly-Gly-Leu Hydrocodone
Cl
HCl

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeSolvent was removed
  2. 2
    Trocknenfinal product dried under vacuum

Vorschrift

To the Boc-Gly-Gly-Leu-Hydrocodone (2.08 g) was added 50 ml of 4N HCl in dioxane. The resulting mixture was stirred at ambient temperatures for 18 hours. Solvent was removed and final product dried under vacuum. Solid was collected as a slightly yellow solid (1.72 g, 86% yield): 1H NMR (DMSO-d6) δ 0.89 (dd, 6H), 1.50-1.87 (m, 5H), 2.26 (m, 2H), 2.66 (m, 2H), 2.82-2.97 (m, 5H), 3.21 (m, 2H), 3.60 (m, 4H), 3.88 (m, 5H), 4.37 (m, 1H), 5.04 (s, 1H), 5.60 (s, 1H), 6.79 (d, 2H), 8.07 (br s, 3H), 8.54 (br s, 1H), 8.66 (br s, 1H), 11.29 (br s, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08343927B2uspto-grants-2013_01