Cyanoacetic acid → 1-(Diphenylmethyl)azetidin-3-yl cyanoacetate

HRID 622675Notes

Reaction equation

HRID 622675 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[CH:7]([N:20]1[CH2:23][CH:22](O)[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([CH2:3][C:4]([O:6][CH:22]1[CH2:23][N:20]([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:21]1)=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 99724351-(Diphenylmethyl)azetidin-3-yl cyanoacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.25 g (0.05 mole) of cyanoacetic acid and 11.95 g (0.05 mole) of 1-benzhydryl-3-hydroxyazetidine were dissolved in 400 ml of tetrahydrofuran. 12.38 g (0.06 mole) of 1,3-dicyclohexylcarbodiimide were then added to the solution, whilst stirring, after which the mixture was stirred at 55° C. for 11 hours. At the end of this time, the mixture was cooled, precipitated crystals were removed and the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate and the resulting solution was washed with water and then dried over anhydrous sodium sulfate.

Workup

  1. stirringafter which the mixture was stirred at 55° C. for 11 hours
  2. temperatureAt the end of this time, the mixture was cooled
  3. customprecipitated crystals
  4. customwere removed
  5. customthe solvent was removed by distillation under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washthe resulting solution was washed with water
  8. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-ea09ae25e221479295cc4eac9e2920d0
Source dataset
uspto-grants-1988_09
Patent number
US04772596

Reaction notes

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