HCID 12362975, compound → (2r,3s)-3-Phenylisoserine amide dibenzoyl-tartaric acid salt

HRID 425956Notes

Reaction equation

HRID 425956 reaction equation
[C:1]1([CH:7]([CH:9]([C:11]([NH2:13])=[O:12])[OH:10])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([C:22]([C:37]([OH:39])=[O:38])([OH:36])[C:23]([C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([OH:27])[C:24]([OH:26])=[O:25])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:28]([C:23]([C:24]([OH:26])=[O:25])([OH:27])[C:22]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([OH:36])[C:37]([OH:39])=[O:38])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:1]1([C@@H:7]([C@H:9]([C:11]([NH2:13])=[O:12])[OH:10])[NH2:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12362975HCID 12362975, compoundHCID 146084173-Phenylisoserine amide

Product 1

HCID 131729427(2r,3s)-3-Phenylisoserine amide dibenzoyl-tartaric acid salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic threo 3-phenylisoserine amide (IX) (120.0 g, 0.67 mole) and (−)-dibenzoyltartaric acid (240.1 g, 0.67 mole) were suspended in ethanol (1080.0 g). The suspension was refluxed for 2 hours, then cooled to room temperature and stirred for further 60 minutes. The product was filtered off, washed with ethanol (400.0 g) and vacuum dried at 50° C. Yield: 180.6 g (0.34 mole, 50%).

Workup

  1. temperatureThe suspension was refluxed for 2 hours
  2. filtrationThe product was filtered off
  3. washwashed with ethanol (400.0 g) and vacuum
  4. customdried at 50° C

Sources & evidence

ORD record
ord-40201be001ab4f0bbdd3ae40ba67ce70
Source dataset
uspto-grants-2012_01
Patent number
US08106231B2

Reaction notes

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