D-Tartaric acid → 17-Cyclobutylmethyl-3-hydroxy-8beta-methylmorphinan-6-one Tartrate

HRID 128213

Reaction equation

HRID 128213 reaction equation
[C:1]([OH:10])(=[O:9])[C@H:2]([C@@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH:11]1([CH2:15][N:16]2[CH2:33][CH2:32][C@@:23]34[C:24]5[CH:25]=[C:26]([OH:31])[CH:27]=[CH:28][C:29]=5[CH2:30][C@@H:17]2[C@@H:18]3[C@@H:19]([CH3:35])[CH2:20][C:21](=[O:34])[CH2:22]4)[CH2:14][CH2:13][CH2:12]1>C(O)C>[C:6]([CH:4]([CH:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[CH:11]1([CH2:15][N:16]2[CH2:33][CH2:32][C@@:23]34[C:24]5[CH:25]=[C:26]([OH:31])[CH:27]=[CH:28][C:29]=5[CH2:30][C@@H:17]2[C@@H:18]3[C@@H:19]([CH3:35])[CH2:20][C:21](=[O:34])[CH2:22]4)[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 5388867717-Cyclobutylmethyl-3-hydroxy-8beta-methylmorphinan-6-one

Product 1

HCID 7052884217-Cyclobutylmethyl-3-hydroxy-8beta-methylmorphinan-6-one Tartrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of d-tartaric acid (16.09, 106 mmole) in ethanol (100 ml) was added dropwise a solution of 17-cyclobutylmethyl-3-hydroxy-8β-methylmorphinan-6-one (TR-5130-free base, 32.0 g, 94 mmole) in ethanol (100 ml). After several minutes of stirring, a white solid began to precipitate. The slurry was stirred at room temperature for several hours and then kept in the cold overnight. The solid was collected, washed with cold ethanol followed by ether and dried at atmospheric pressure and 115° C. for one hour to give 32.0 g (69%) of TR-5257 as a white powder, mp. 210°-213° dec.

Workup

  1. customto precipitate
  2. stirringThe slurry was stirred at room temperature for several hours
  3. customkept in the cold overnight
  4. customThe solid was collected
  5. washwashed with cold ethanol
  6. customdried at atmospheric pressure and 115° C. for one hour
  7. customto give 32.0 g (69%) of TR-5257 as a white powder, mp. 210°-213° dec.

Sources & evidence

ORD record
ord-3082894a3de041108a4101f472094825
Source dataset
uspto-grants-1981_03
Patent number
US04259329

Linked notes

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