L-Tartaric acid → ABT-288 tartrate

HRID 12958

Reaction equation

HRID 12958 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH3:11][N:12]1[CH2:19][C@@H:18]2[C@@H:14]([N:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]5)=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:17]2)[CH2:13]1>O.C(O)C>[C:6]([C@@H:4]([C@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[CH3:11][N:12]1[CH2:19][C@@H:18]2[C@@H:14]([N:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([N:32]5[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]5)=[CH:28][CH:27]=4)=[CH:22][CH:21]=3)[CH2:16][CH2:17]2)[CH2:13]1

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 24743471Abt-288

Product 1

HCID 68494919ABT-288 tartrateYield 94.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.45 g of L-tartaric acid (1.07 eq.) in 56 g of water was added to a flask containing a slurry of 8.00 g of the product of Example 41G in anhydrous ethanol (44 g). The mixture was heated under reflux and after 30 minutes most solids had dissolved. The mixture was cooled at 5° C. per hour to 60° C., and then allowed to cool to ambient temperature overnight. After cooling the mixture to −15° C. the product slurry was filtered and dried at 45-50° C. overnight to provide the title compound (10.64 g, 94.8%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux and after 30 minutes most solids
  3. dissolutionhad dissolved
  4. temperatureThe mixture was cooled at 5° C. per hour to 60° C.
  5. temperatureAfter cooling the mixture to −15° C. the product slurry
  6. filtrationwas filtered
  7. customdried at 45-50° C. overnight

Sources & evidence

ORD record
ord-280903f9ca7f44478fc336a12a028594
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Linked notes

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