Butanal → AzeOH D-tartrate

HRID 1857047Notes

Reaction equation

HRID 1857047 reaction equation
[NH:1]1[CH2:7][CH2:6][CH: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)C>[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 17288Azetidinecarboxylic AcidHCID 439655D-Tartaric acid

Product 1

HCID 131721350AzeOH D-tartrateYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

DL-AzeOH (6.14 g; 60.8 mmol) was dissolved in acetic acid (36.5 mL) at 85° C. Butyric aldehyde (0.49 g; 6.8 mmol) and D-tartaric acid (9.12 g; 60.8 mmol) were added and the mixture maintained at 85° C. for 6 hours. The reaction mixture was then gradually cooled to 0 C. The crystalline product was filtered off, washed with acetic acid and dried to yield 13.78 g (90%) of L-AzeOH-D-tartrate with a d.e. of 89%. Recrystallisation 13.78 g of the diastereomeric salt from dissolved acetic acid:water (9:1; 124 mL) yielded 11.08 g of L-AzeOH-D-tartrate with a d.e. of 99.8%.

Workup

  1. temperatureThe reaction mixture was then gradually cooled to 0 C
  2. filtrationThe crystalline product was filtered off
  3. washwashed with acetic acid
  4. customdried

Sources & evidence

ORD record
ord-57511efcaf93497e9457f6dcc1cc994c
Source dataset
uspto-grants-2000_11
Patent number
US06143903

Reaction notes

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