Hydrochloric Acid → HCID 131727059, compound

HRID 32335Notes

Reaction equation

HRID 32335 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 (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-60a37d204cb04304ac95197a380cf8b0
Source dataset
uspto-grants-2008_09
Patent number
US07427600B2

Reaction notes

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