HCID 86741247, compound → HCID 70434617, compound

HRID 980958Notes

Reaction equation

HRID 980958 reaction equation
Cl[CH:2]1[N:5]([C:6](=[C:11]2[S:15][C:14]([C:17]([F:20])([F:19])[F:18])([OH:16])[CH2:13][S:12]2)[C:7]([O:9][CH3:10])=[O:8])[C:4](=[O:21])[CH2:3]1>C(Cl)Cl.C(N(CC)CC)C>[OH2:8].[F:18][C:17]([F:20])([F:19])[C:14](=[O:16])[CH2:13][S:12][C:11]1[S:15][C@@H:2]2[CH2:3][C:4](=[O:21])[N:5]2[C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 86741247HCID 86741247, compound

Product 1

HCID 70434617HCID 70434617, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Sulphuryl chloride (59.7 mg, 35.8 μl, 0.442 mmole) was added to a solution of methyl 2-(4-methylthio-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate (166 mg, 0.442 mmole) in methylene chloride (3 ml) at room temperature, with stirring. After this addition, the solution was stirred for 3 minutes and then the solvent was distilled off to give the crude methyl 2-(4-chloro-2-azetidinon-1-yl)-2-(4-trifluoromethyl-4-hydroxy-1,3-dithiolan-2-ylidene)acetate. This 4-chloroazetidinone compound was dissolved in methylene chloride (3 ml) without purification, and triethylamine (185 μl) was added thereto, after which the mixture was stirred at room temperature for 2 hours. The solvent was distilled off from the reaction mixture under reduced pressure. The resulting residue was dissolved in ethyl acetate and washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off under reduced pressure and the residue was purified by preparative thin layer chromatography (eluent: a 3:2 by volume mixture of benzene and ethyl acetate), to give 63 mg of the desired product as crystals.

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off from the reaction mixture under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washwashed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by preparative thin layer chromatography (eluent
  8. additiona 3:2 by volume mixture of benzene and ethyl acetate),

Sources & evidence

ORD record
ord-9f27a9fc2c4b477fbc9ad5a72a176e34
Source dataset
uspto-grants-1987_01
Patent number
US04639441

Reaction notes

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