Sodium Hydroxide → Morphine 6-glucuronide

HRID 53869Notes

Reaction equation

HRID 53869 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([C:11]([O-:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[OH-].[Na+].N.O.[CH:18]1[C:34]2[CH2:33][C@H:32]3[N:35]([CH2:37][CH2:38][C@@:24]45[C@H:31]3[CH:30]=[CH:29][C@H:27](O)[C@@H:25]4[O:26][C:22]([C:23]=25)=[C:20]([OH:21])[CH:19]=1)[CH3:36]>CO.C(O)(=O)C.CCCCO.CC(C)=O.CC(O)=O>[CH3:36][N:35]1[C@@H:32]2[CH2:33][C:34]3=[CH:18][CH:19]=[C:20]([OH:21])[C:22]4[O:26][C@H:25]5[C@@H:27]([O:1][C@@H:2]6[O:10][C@H:9]([C:11]([OH:13])=[O:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]6[OH:4])[CH:29]=[CH:30][C@@H:31]2[C@:24]5([C:23]=43)[CH2:38][CH2:37]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5288826MorphineHCID 5460126aldehydo-D-glucuronateHCID 12896473Azane;hydrate

Product 1

HCID 5360621Morphine 6-glucuronideYield 52%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 86750706n-BuOH acetone AcOHSolvent

Procedure

To a solution of the above glucuronate in MeOH (24 ml) was added 5% aqueous NaOH (6 ml) and the mixture was left to stir for 20 hours. T.l.c (n-BuOH/acetone/AcOH/5% aq.NH3 /water 45:15:10:10:20) showed that there were two components one of which was M6G and the other morphine. The solution was transferred to a beaker and was acidified with glacial acetic acid (7 ml) which took the pH of the mixture to 5.5. Shortly after this pH was reached (5 minutes), a white solid started to precipitate. The suspension was stirred for a further 30 minutes, the solid filtered and washed with MeOH, and morphine-6-glucuronide (0.4 g, 52%) was obtained after drying at 120° C. for 4 hours, m.p. 240°-243° C. More M6G could be obtained by cooling the filtrate.

Workup

  1. waitthe mixture was left
  2. custom(5 minutes)
  3. customto precipitate
  4. stirringThe suspension was stirred for a further 30 minutes
  5. filtrationthe solid filtered
  6. washwashed with MeOH

Sources & evidence

ORD record
ord-5a44e8790619407d8231ff3ebcf9fef6
Source dataset
uspto-grants-1997_04
Patent number
US05621087

Reaction notes

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