L-Tartaric acid → Tartrate

HRID 1967442Notes

Reaction equation

HRID 1967442 reaction equation
[CH3:1][N:2]1[CH2:11][C@@H:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([C:22]3[N:27]=[N:26][C:25]([NH2:28])=[CH:24][CH:23]=3)=[CH:7][CH:8]=2)[CH2:3]1.[C:29]([OH:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CO.O>[C:34]([C@@H:32]([C@H:30]([C:29]([O-:38])=[O:37])[OH:31])[OH:33])([O-:36])=[O:35].[CH3:1][N:2]1[CH2:11][C@@H:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([C:22]3[N:27]=[N:26][C:25]([NH2:28])=[CH:24][CH:23]=3)=[CH:7][CH:8]=2)[CH2:3]1

Participants

6

Reactant 2

HCID 444305L-Tartaric acidHCID 58212050Liafensine

Product 2

HCID 119400TartrateHCID 58212050Liafensine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Alternative procedure: To a slurry of Compound 2, free base (1.5 g, 4.1 mmol) in methanol (80 mL) was added a solution of L-tartaric acid (0.63 g, 4.2 mmol) in methanol (15 mL) and water (10 mL). The reaction slurry became a clear solution after heating under reflux. The resulting solution was then cooled to 0° C. while stirring and precipitation occurred. The precipitate obtained was collected by filtration. This solid was re-crystallized twice from methanol (150 mL) and water (20 mL). The resulting solid was dissolved in methanol (25 mL) and water (100 mL), and the solution was lyophilized to give the L-tartrate salt of Compound 2, (1.4 g, 65%, AUC HPLC>99%) as a white solid: [α]23D +79.1° (c 0.15, methanol); 1H NMR (500 MHz, CDCl3) δ 7.87-7.80 (m, 6H), 7.69 (dd, J=8.0, 1.5 Hz, 1H), 7.51-7.48 (m, 2H), 7.30 (dd, J=8.5, 1.5 Hz, 1H), 7.04-7.01 (m, 2H), 4.71 (dd, J=11.0, 5.5 Hz, 1H), 4.43 (s, 2H), 4.39 (d, J=16.0 Hz, 1H), 4.29 (d, J=15.5 Hz, 1H), 3.64(dd, J=11.5, 5.5 Hz, 1H), 3.37-3.30 (m, 1H), 2.85 (s, 3H); ESI MS m/z 367 [M+H]+.

Workup

  1. temperatureafter heating
  2. temperatureunder reflux
  3. customprecipitation
  4. customThe precipitate obtained
  5. filtrationwas collected by filtration
  6. customThis solid was re-crystallized twice from methanol (150 mL) and water (20 mL)
  7. dissolutionThe resulting solid was dissolved in methanol (25 mL)

Sources & evidence

ORD record
ord-d8d6974658384fed89e11c91e7bdafb2
Source dataset
uspto-grants-2013_04
Patent number
US08420811B2

Reaction notes

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