Hydrochloric Acid → HCID 131726872, compound

HRID 1943978Notes

Reaction equation

HRID 1943978 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])=[O:4].[CH3:25][N:26]1[C@@H:43]2[CH2:44][C:31]3[CH:32]=[CH:33][C:34]([O:45][CH3:46])=[C:35]4[O:36][C@H:37]5[C:38]([CH2:40][CH2:41][C@@H:42]2[C@:29]5([C:30]=34)[CH2:28][CH2:27]1)=[O:39].Cl>O1CCOCC1>[CH3:14][CH:12]([CH2:11][C@H:10]([NH:9][C:7]([CH2:6][NH:5][C:3]([CH2:2][NH2:1])=[O:4])=[O:8])[C:15]([OH:17])=[O:16])[CH3:13].[CH3:25][N:26]1[C@@H:43]2[CH2:44][C:31]3[CH:32]=[CH:33][C:34]([O:45][CH3:46])=[C:35]4[O:36][C@H:37]5[C:38]([CH2:40][CH2:41][C@@H:42]2[C@:29]5([C:30]=34)[CH2:28][CH2:27]1)=[O:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131726873HCID 131726873, compound

Product 1

HCID 131726872HCID 131726872, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  1. customSolvent was removed
  2. dry with materialfinal product dried under vacuum

Sources & evidence

ORD record
ord-5ca82b7db9af428ca572fc98f9bfd02a
Source dataset
uspto-grants-2013_03
Patent number
US08394813B2

Reaction notes

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