Ethanol → (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;(2R,3R)-2,3-dihydroxybutanedioic acid;hydrate

HRID 1602587Notes

Reaction equation

HRID 1602587 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].[CH:23]([OH:32])([C:29]([OH:31])=[O:30])[CH:24]([OH:28])[C:25]([OH:27])=[O:26].C([OH:35])C>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].[C@H:23]([OH:32])([C:29]([OH:31])=[O:30])[C@@H:24]([OH:28])[C:25]([OH:27])=[O:26].[OH2:35]

Participants

4

Reactant 2

HCID 702EthanolHCID 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 5463978(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;(2R,3R)-2,3-dihydroxybutanedioic acid;hydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A sample of 149.4 g of hydrocodone bitartrate containing 2.1 wt % of ethanol was placed in a crystallisation dish. The sample was placed in a vacuum oven along with a crystallisation dish containing water (ca 200 ml). A vacuum was applied (16665 pascals (approximately 10 mm to 1 mm Hg)) and the sample was dried at 60° C. for 24 hours to afford 151.7 g of ethanol-free (as defined below) product. The water content measured by Karl Fisher titration was 9.66% which indicated that the final product was a hemi-pentahydrate.

Workup

  1. customthe sample was dried at 60° C. for 24 hours
  2. customto afford 151.7 g of ethanol-free (as defined below) product

Sources & evidence

ORD record
ord-7f64737a9b324716abf769eab3f721b4
Source dataset
uspto-grants-1999_11
Patent number
US05981751

Reaction notes

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