2,3-Dihydroxybutanedioic Acid → HCID 729944, compound

HRID 1723707Notes

Reaction equation

HRID 1723707 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](O)(=[O:17])[CH:10]([CH:12]([C:14](O)=[O:15])[OH:13])[OH:11]>C1(C)C(C)=CC=CC=1>[CH2:1]([N:8]1[C:14](=[O:15])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C:9]1=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 7504Benzylamine

Product 1

HCID 729944HCID 729944, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Benzylamine (75 g, 0.70 mol) and (−)-tartaric acid (100 g, 700 mol) were heated in boiling xylene (1.0 L) in a Dean-Stark apparatus. After cooling, the product was collected, washed with acetone, and recrystallized from EtOH to afford the product (120 g, 77%). 1H NMR (300 MHz, CDCl3) δ 7.39-7.20 (5H, m), 6.27 (2H, d), 4.58 (1H, d), 4.52 (1H, d), 4.38 (2H, m).

Workup

  1. temperatureAfter cooling
  2. customthe product was collected
  3. washwashed with acetone
  4. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-31329337faf5449bb3a62378714cfb2d
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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