Hydrochloric Acid → HCID 131727059, compound

HRID 1436991Notes

Reaction equation

HRID 1436991 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([NH:17][C@H:18]([C:23]([OH:25])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])=[O:12])=[O:8])=[O:4].[CH3:33][N:34]1[C@@H:51]2[CH2:52][C:39]3[CH:40]=[CH:41][C:42]([O:53][CH3:54])=[C:43]4[O:44][C@H:45]5[C:46]([CH2:48][CH2:49][C@@H:50]2[C@:37]5([C:38]=34)[CH2:36][CH2:35]1)=[O:47].Cl>O1CCOCC1>[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([NH:17][C@H:18]([C:23]([OH:25])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])=[O:12])=[O:8])=[O:4].[CH3:33][N:34]1[C@@H:51]2[CH2:52][C:39]3[CH:40]=[CH:41][C:42]([O:53][CH3:54])=[C:43]4[O:44][C@H:45]5[C:46]([CH2:48][CH2:49][C@@H:50]2[C@:37]5([C:38]=34)[CH2:36][CH2:35]1)=[O:47]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131727061HCID 131727061, compound

Product 1

HCID 131727059HCID 131727059, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the Boc-Gly-Gly-Gly-Gly-Leu-Hydrocodone (SEQ ID NO: 1) (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).

Workup

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

Sources & evidence

ORD record
ord-69b01640945941fbad3d328370ab140f
Source dataset
uspto-grants-2009_11
Patent number
US07622441B2

Reaction notes

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