Water → HCID 11687363, compound

HRID 1953173Notes

Reaction equation

HRID 1953173 reaction equation
[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][C@H:10]1[C:13]([O:15]C)=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.C(C(CCCC)C(O)=O)C>CCCCCCC>[CH3:1][C@H:2]([N:9]1[CH2:12][CH2:11][C@H:10]1[C:13]([OH:15])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86972-Ethylhexanoic AcidHCID 10998528methyl (2S)-1-[(1S)-1-phenylethyl]azetidine-2-carboxylate

Product 1

HCID 11687363HCID 11687363, compoundYield 400.8%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl N-[(S)-methylbenzyl]azetidine-2-(s)-carboxylate (161.6 g) and water (323 g) was added 2-ethylhexanoic acid (116.9 g) and resulting mixture was stirred at 60° C. for about 12 hours. Heptane (161 g) was added to the reaction mixture and separated. The organic layer was extracted with water (80 g). Combined water layer was washed with heptane (161.6 g×3) to give aqueous N-[(S)-methylbenzyl]azetidine-2-(S)-carboxylic acid solution (606.2 g). Yield 94%.

Workup

  1. customresulting mixture
  2. customseparated
  3. extractionThe organic layer was extracted with water (80 g)
  4. washCombined water layer was washed with heptane (161.6 g×3)

Sources & evidence

ORD record
ord-b741fb9f74744ce796465f81515da351
Source dataset
uspto-grants-2000_09
Patent number
US06114543

Reaction notes

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