2,6-Lutidine → p-Nitrobenzyl 2-(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 2291001Notes

Reaction equation

HRID 2291001 reaction equation
[CH2:1]([S:3][CH:4]1[N:7]([CH:8](O)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH:5]1[CH2:24][CH2:25][O:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28])[CH3:2].N1C(C)=CC=CC=1C.S(Cl)([Cl:50])=O>O1CCCC1>[CH2:1]([S:3][CH:4]1[N:7]([CH:8]([Cl:50])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH:5]1[CH2:24][CH2:25][O:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)=[O:28])[CH3:2]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 54314145p-Nitrobenzyl 2(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-hyroxyacetate

Product 1

HCID 88644849p-Nitrobenzyl 2-(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-chloroacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 11.3 g p-nitrobenzyl 2(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-hyroxyacetate and 3.02 ml 2,6-lutidine in 175 ml anhydrous tetrahydrofuran was cooled to 0° C. under a nitrogen atmosphere. Thionyl chloride (1.75 ml) was added dropwise and the resulting mixture was stirred at 0° C. for 20 min. The mixture was filtered through Supercel and the filtrate was concentrated in vacuo. The concentrate was dissolved in methylene chloride and the resulting solution was washed successively with 200 ml 1N aqueous hydrochloric acid, 200 ml saturated aqueous sodium bicarbonate solution and 200 ml saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil (11.6 g) of the title compound. The NMR spectrum of the title compound in deuterochloroform showed peaks at 1.04-1.6 (c, 6H); 2.6 (m, 2H); 3.4 (m, 1H); 4.8-5.4 (c, 6H); 5.85, 5.9, 5.98, 6.1 (s, 1H); 7.5 (m, 4H); 8.2 (m, 4H) ppm.

Workup

  1. filtrationThe mixture was filtered through Supercel
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe concentrate was dissolved in methylene chloride
  4. washthe resulting solution was washed successively with 200 ml 1N aqueous hydrochloric acid, 200 ml saturated aqueous sodium bicarbonate solution and 200 ml saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to an oil (11.6 g) of the title compound

Sources & evidence

ORD record
ord-3b3949f6bbe44deaaafcf232664ab644
Source dataset
uspto-grants-1986_10
Patent number
US04619783

Reaction notes

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