2-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

HRID 2291003

Reaction equation

HRID 2291003 reaction equation
[CH2:1]([S:3][CH:4]1[NH:7][C:6](=[O:8])[CH2:5]1)[CH3:2].C([O:11][CH:12](O)[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])C>C1C=CC=CC=1>[CH2:1]([S:3][CH:4]1[N:7]([CH:12]([OH:11])[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[O:14])[C:6](=[O:8])[CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 110433162-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl esterHCID 140503764-Ethylthio-2-oxoazetidine

Product 1

HCID 14050377p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 12.3 g. of 4-ethylthio-2-oxoazetidine and 25.5 g. of p-nitrobenzyl glyoxylate ethyl hemiacetal in 900 ml. of benzene was heated under reflux for 16 hours. During the heating for 16 hours, water and ethanol were removed from the reaction mixture by azeotropic distillation using a Dean-Stark trap. At this point, the benzene was removed by evaporation in vacuo, and the residue was dissolved in 700 ml. of dichloromethane. The dichloromethane solution was washed three times with water, and then dried with anhydrous sodium sulfate. Evaporation in vacuo afforded 32.5 g of the title compound as a yellow semi-solid. The IR spectrum of the product in chloroform showed an absorption at 5.65 microns. The NMR spectrum of the product in deuterochloroform showed peaks at 1.25 (t, 3H); 2.35-3.62 (m, 4H); 4.3 (s, 1H); 4.85 (m, 1H); 5.22 and 5.54 (ss, 1H); 5.38 (s, 2H); 7.5 (d, 2H); and 8.2 (d, 2H) ppm.

Workup

  1. temperatureunder reflux for 16 hours
  2. customwater and ethanol were removed from the reaction mixture by azeotropic distillation
  3. customAt this point, the benzene was removed by evaporation in vacuo
  4. dissolutionthe residue was dissolved in 700 ml
  5. washThe dichloromethane solution was washed three times with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customEvaporation in vacuo

Sources & evidence

ORD record
ord-9c6dc37acb294861a7a8376d05451720
Source dataset
uspto-grants-1986_10
Patent number
US04619783

Linked notes

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