1-Chloroethyl chloroformate → Methyl azetidin-3-ylidene(3,5-difluorophenyl)acetate

HRID 602670Notes

Reaction equation

HRID 602670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[C:14]2[CH2:17][N:16](C(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:15]2)[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.ClC(OC(Cl)C)=O>C1COCC1>[NH:16]1[CH2:17][C:14](=[C:9]([C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:15]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 57559921Methyl (3,5-difluorophenyl)[1-(diphenylmethyl)azetidin-3-ylidene]acetate

Product 1

HCID 67065925Methyl azetidin-3-ylidene(3,5-difluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.405 g (1 mmol) of methyl (3,5-difluorophenyl)[1-(diphenylmethyl) azetidin-3-ylidene]acetate in 2 mL of dry THF was added 0.284 g (2 mmol) of 1-chloroethyl chloroformate and the solution was stirred at room temperature. After 1 h, the solution was concentrated and the residue was triturated with 2 mL of 10% ether-hexane. This was decanted and the solid residue was dissolved in methanol and heated to reflux for 6 h. The solution was concentrated to afford the title compound as the hydrochloride salt: Mass Spectrum: m/e=240 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was triturated with 2 mL of 10% ether-hexane
  3. customThis was decanted
  4. dissolutionthe solid residue was dissolved in methanol
  5. temperatureheated
  6. temperatureto reflux for 6 h
  7. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-868dae4e405a4eb7bf1c4b9c790a3b8b
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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