Reaction #1885024

ord-64dbd5b485ae49abbf21a14f04f8fc21

Reaction equation

COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314.C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O
Boc-Ala-Pro Hydrocodone
Cl
HCl
→
COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314.C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O
solid
COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314.C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O
Ala-Pro Hydrocodone

Reactants

COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314.C[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O
Boc-Ala-Pro 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-Ala-Pro-Hydrocodone (0.100 g) was added 10 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 (0.56 g, 71% yield): 1H NMR (DMSO-d6) δ 1.38 (s, 3H), 1.48 (t, 1H), 1.80-2.29 (m, 8H), 2.65 (m, 1H), 2.80 (s, 3H), 2.96 (m, 3H), 3.23 (m, 2H), 3.76 (s, 3H), 3.92 (s, 1H), 4.22 (s, 1H), 4.53 (s, 1H), 5.00 (s, 1H), 5.84 (d, 1H), 6.77 (d, 1H), 6.86 (d, 1H), 8.25 (br s, 3H).

Source

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