Reaction #1885030

ord-580879e8b45548b18d271cf955daa3fd

Reaction equation

CC(C)C[C@H](NC(=O)CNC(=O)CNC(=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-Gly-Gly-Leu Hydrocodone
Cl
HCl
→
CC(C)C[C@H](NC(=O)CNC(=O)CNC(=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
Yield 97.0%
CC(C)C[C@H](NC(=O)CNC(=O)CNC(=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-Gly-Gly-Leu Hydrocodone
Yield 97.0%

Reactants

CC(C)C[C@H](NC(=O)CNC(=O)CNC(=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-Gly-Gly-Leu Hydrocodone
Cl
HCl

Reagents

None

Solvents

C1COCCO1
dioxane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherSolvent was removed
  2. 2
    Dryingfinal product dried under vacuum

Procedure

To the Boc-Gly-Gly-Gly-Gly-Leu-Hydrocodone (0.304 g) was added 25 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 (0.247 g, 97% yield): 1H NMR (DMSO-d6) δ 0.87 (m, 6H), 1.23 (s, 1H), 1.51-1.86 (m, 4H), 2.18 (m, 1H), 2.71 (m, 2H), 2.77 (s, 3H), 2.96 (m, 2H), 3.17 (m, 2H), 3.61 (s, 3H), 3.81-3.84 (m, 10H), 4.22 (m, 1H), 4.36 (m, 1H), 5.09 (m, 1H), 5.59 (d, 1H), 6.74 (dd, 2H), 8.16 (br s, 4H), 8.38 (br s, 1H), 8.74 (br s, 1H), 11.42 (br s, 1H).

Source

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