Butanal → D-AzeOH L-tartrate

HRID 1857045Notes

Reaction equation

HRID 1857045 reaction equation
[NH:1]1[CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].CCCC=O.[C:13]([OH:22])(=[O:21])[C@@H:14]([C@H:16]([C:18]([OH:20])=[O:19])[OH:17])[OH:15]>C(O)=O>[NH:1]1[CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[C:18]([C@@H:16]([C@H:14]([C:13]([O-:22])=[O:21])[OH:15])[OH:17])([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 261ButanalHCID 16486L-Azetidine-2-carboxylic acidHCID 444305L-Tartaric acid

Product 1

HCID 131721351D-AzeOH L-tartrateYield 18.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

L-AzeOH (99% e.e.; 1.01 g; 10 mmol) was dissolved in formic acid (4 mL) at 80° C. Butyric aldehyde (0.072 g; 1.0 mmol) was added and the mixture heated at 90° C. for 3 hours. The solvent was subsequently distilled (45° C.; 4 mbar) and the residue dried under vacuum. The residue was subsequently dissolved in a mixture of ethanol:water (35.6: 29.1) at 76° C. L-Tartaric acid (1.5 g; 10 mmol) was added, the insoluble compounds were filtered off and the solution was cooled to 0° C. The crystalline product was filtered, washed and dried under vacuum to yield 0.45 g of D-AzeOH-L-tartrate with a d.e. of 75%.

Workup

  1. distillationThe solvent was subsequently distilled (45° C.; 4 mbar)
  2. customthe residue dried under vacuum
  3. dissolutionThe residue was subsequently dissolved in a mixture of ethanol:water (35.6: 29.1) at 76° C
  4. filtrationthe insoluble compounds were filtered off
  5. temperaturethe solution was cooled to 0° C
  6. filtrationThe crystalline product was filtered
  7. washwashed
  8. customdried under vacuum

Sources & evidence

ORD record
ord-908c2a2802d649048a5489b67fc80a95
Source dataset
uspto-grants-2000_11
Patent number
US06143903

Reaction notes

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