Hydrochloric Acid → HCID 131726786, compound

HRID 1436990Notes

Reaction equation

HRID 1436990 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[CH3:21][N:22]1[C@@H:39]2[CH2:40][C:27]3[CH:28]=[CH:29][C:30]([O:41][CH3:42])=[C:31]4[O:32][C@H:33]5[C:34]([CH2:36][CH2:37][C@@H:38]2[C@:25]5([C:26]=34)[CH2:24][CH2:23]1)=[O:35].Cl>O1CCOCC1>[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[CH3:21][N:22]1[C@@H:39]2[CH2:40][C:27]3[CH:28]=[CH:29][C:30]([O:41][CH3:42])=[C:31]4[O:32][C@H:33]5[C:34]([CH2:36][CH2:37][C@@H:38]2[C@:25]5([C:26]=34)[CH2:24][CH2:23]1)=[O:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131726787HCID 131726787, compound

Product 1

HCID 131726786HCID 131726786, compoundYield 675.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the Boc-Ala-Pro-Hydrocodone (0.100 g) was added 10 mil 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).

Workup

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

Sources & evidence

ORD record
ord-f7f5f9b387514e84ab9c4882ce700040
Source dataset
uspto-grants-2009_11
Patent number
US07622441B2

Reaction notes

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