L-Tartaric acid → HCID 69555050, compound

HRID 428896Notes

Reaction equation

HRID 428896 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2.[C:28]([OH:37])(=[O:36])[C@@H:29]([C@H:31]([C:33]([OH:35])=[O:34])[OH:32])[OH:30]>>[C:33]([C@@H:31]([C@H:29]([C:28]([OH:37])=[O:36])[OH:30])[OH:32])([OH:35])=[O:34].[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6]2

Participants

3

Reactant 2

HCID 444305L-Tartaric acidHCID 9864893HCID 9864893, compound

Product 1

HCID 69555050HCID 69555050, compoundYield 50.4%

Conditions

Temperature
10 °C

Procedure

A solution of N-(3-{6-methyl-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Example 1, 2.00 g, 5.2 mmol) in Industrial Methylated Spirits (20 ml) was heated under reflux. To the solution was added L-tartaric acid (0.86 g, 5.8 mmol) and the reaction mixture was heated under reflux for 30 min before cooling to 10° C. over a 2 h period. The resulting precipitate was collected by filtration to afford the title compound as a white solid (1.40 g, 50%).

Workup

  1. temperatureunder reflux
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 30 min
  4. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-107c3c76717247c794e959ba4b066cf1
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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