تفاعل #1885030

ord-580879e8b45548b18d271cf955daa3fd

معادلة التفاعل

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
المردود 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
المردود 97.0%

المتفاعلات

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

الكواشف

لا شيء

المذيبات

C1COCCO1
dioxane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىSolvent was removed
  2. 2
    تجفيفfinal product dried under vacuum

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08343927B2uspto-grants-2013_01