Reaction #82147

ord-5a44e8790619407d8231ff3ebcf9fef6

Reaction equation

CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
morphine
N.O
NH3 water
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)[O-]
glucuronate
[Na+].[OH-]
NaOH
→
CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C=C[C@H]3[C@H]1C5
morphine-6-glucuronide
Yield 52.0%

Reactants

CN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5
morphine
N.O
NH3 water
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)[O-]
glucuronate
[Na+].[OH-]
NaOH

Reagents

None

Solvents

CC(=O)O
acetic acid
CC(=O)O.CC(C)=O.CCCCO
n-BuOH acetone AcOH
CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.WAITthe mixture was left
  2. 2
    Other(5 minutes)
  3. 3
    Otherto precipitate
  4. 4
    workup.STIRRINGThe suspension was stirred for a further 30 minutes
  5. 5
    Filtrationthe solid filtered
  6. 6
    Washwashed with MeOH

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05621087uspto-grants-1997_04