Oxalyl chloride → p-Nitrobenzyl 2-(4-chloro-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

HRID 1982146Notes

Reaction equation

HRID 1982146 reaction equation
C(S([CH:5]1[N:8]([C:9](=[C:23]([S:30][C:31](=[O:33])[CH3:32])[S:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:34])[CH2:6]1)=O)C.C(Cl)(=O)C([Cl:38])=O>C(Cl)Cl>[Cl:38][CH:5]1[N:8]([C:9](=[C:23]([S:30][C:31](=[O:33])[CH3:32])[S:24][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C:7](=[O:34])[CH2:6]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 53818988p-Nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Product 1

HCID 54496834p-Nitrobenzyl 2-(4-chloro-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)acrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.2 g p-nitrobenzyl 2-(4-ethylsulfinyl-2-oxo-1-azetidinyl)-3-acetylthio-3-(2-ethoxyethylthio)-acrylate in 50 ml methylene chloride was cooled to -50° C. under a nitrogen atmosphere. Oxalyl chloride (0.196 ml) was added dropwise at -50° C., then the reaction mixture was allowed to warm to -15°. After 1 hour at -15° C. the methylene chloride solution was washed with 20 ml saturated aqueous sodium bicarbonate solution and 20 ml water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil (1.2 g). The crude title compound was used without further purification. The NMR spectrum of a deuterochloroform solution showed peaks at 1.23(m,3H); 2.3-3.72(c,11H); 5.23(m,2H); 5.7-6.32(c,1H); 7.52(m,2H); and 8.2(m,2H) ppm. The infrared spectrum of a chloroform solution had absorption bands at 5.6 and 5.78 microns.

Workup

  1. temperatureto warm to -15°
  2. washAfter 1 hour at -15° C. the methylene chloride solution was washed with 20 ml saturated aqueous sodium bicarbonate solution and 20 ml water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to an oil (1.2 g)
  5. customThe crude title compound was used without further purification
  6. customabsorption bands at 5.6 and 5.78 microns

Sources & evidence

ORD record
ord-594e9b3af6db4e2281854b9d8e8438da
Source dataset
uspto-grants-1986_06
Patent number
US04595539

Reaction notes

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