Réaction #1552115

ord-f3cc179d4b6f4a0e84a26f3e520526b6

Équation de réaction

O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O
D-glucuronic acid
C[C@H]1CNCCc2ccc(Cl)cc21
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
CC(C)=O
acetone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O
D-glucuronic acid
→
C[C@H]1CNCCc2ccc(Cl)cc21.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O
(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt

Réactifs

O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O
D-glucuronic acid
C[C@H]1CNCCc2ccc(Cl)cc21
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
CC(C)=O
acetone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O
D-glucuronic acid

Réactifs

Aucun

Solvants

CC(C)O
isopropanol
CC#N
acetonitrile
CCOC(C)=O
ethyl acetate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwas added dropwise with vigorous stirring
  2. 2
    AutrePrecipitation
  3. 3
    Températureto cool
  4. 4
    FiltrationThe resulting solid was recovered by filtration
  5. 5
    Autredried in a fume hood overnight
  6. 6
    Autreby DSC of about 164° C.

Mode opératoire

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt was prepared by addition of a molar equivalent of D-glucuronic acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in isopropanol, acetonitrile, ethyl acetate, or acetone at 60° C. D-glucuronic acid, dissolved in the corresponding solvent at 60° C., was added dropwise with vigorous stirring. Precipitation occurred immediately and the suspension was allowed to cool and stir overnight. The resulting solid was recovered by filtration and dried in a fume hood overnight. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine glucuronate salt had an extrapolated melting onset temperature by DSC of about 164° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08999970B2uspto-grants-2015_04