(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic acid → Hydrocodone

HRID 333517

Reaction equation

HRID 333517 reaction equation
[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15].C(O)(C(O)=O)C(O)C(O)=O>O>[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3[CH:8]=[CH:9][C:10]([O:21][CH3:22])=[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=34)[CH2:4][CH2:3]1)=[O:15]

Participants

3

Reactant 1

HCID 20831824(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one;2,3-dihydroxybutanedioic acid

Product 1

HCID 5284569Hydrocodone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The Hydrocodone Resin Complex was prepared by first dissolving 450 g of hydrocodone Bitartrate in 8 kg of purified water, and then slowly adding 1,407 g of AMBERLITE™ IRP-69 resin with continuous mixing. The dispersion was mixed for 4 hours and upon completion, allowed to settle before decanting the supernatant. The slurring/decanting process was repeated twice with sufficient amounts of purified water. The wet resin complex was then dried in a VWR™ convection oven maintained at 50° C. until moisture content was about 20-25%. KOLLICOAT™ SR-30D polymer (500 g) was then slowly added to the wet resin complex in a Hobart type mixer (Kitchen Aid) to form a uniform mass. The wet mass was again dried in a 50° C. VWR™ convection oven to the moisture content around 15-20%. The semi-dried granules were then milled through a 40 mesh screen using CO-MIL™ brand mill and continued drying under 50° C. until the moisture content was between 3-7%. The dried granules were then milled through a 40 mesh screen using CO-MIL™ brand mill.

Workup

  1. additionslowly adding 1,407 g of AMBERLITE™
  2. additionThe dispersion was mixed for 4 hours and upon completion
  3. custombefore decanting the supernatant
  4. customThe wet resin complex was then dried in a VWR™ convection oven
  5. additionKOLLICOAT™ SR-30D polymer (500 g) was then slowly added to the wet resin complex in a Hobart type mixer (Kitchen Aid)
  6. customto form a uniform mass
  7. customThe wet mass was again dried in a 50° C
  8. customThe semi-dried granules were then milled through a 40 mesh screen
  9. customcontinued drying under 50° C. until the moisture content
  10. customThe dried granules were then milled through a 40 mesh screen

Sources & evidence

ORD record
ord-69fec081b0224372a48618b5c731402b
Source dataset
uspto-grants-2014_11
Patent number
US08883217B2

Linked notes

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