Pyridine → p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 426462Notes

Reaction equation

HRID 426462 reaction equation
[C:1]([S:4][CH:5]1[N:8]([CH:9](O)[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:24])[CH2:6]1)(=[O:3])[CH3:2].N1C=CC=CC=1.S(Cl)([Cl:33])=O>O1CCCC1>[C:1]([S:4][CH:5]1[N:8]([CH:9]([Cl:33])[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:24])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl Chloride2×HCID 13132061HCID 13132061, compound

Product 1

HCID 13132062p-Nitrobenzyl 2-(4-Acetylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (-10°) and stirred solution of p-nitrobenzyl 2-(4-acetylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate (102 g., 0.250 mole) in tetrahydrofuran (2000 ml.) were added in succession pyridine (27.1 ml., 0.287 mole) and thionyl chloride (25.2 ml., 0.287 mole); the thionyl chloride addition was done over ca 15 minutes. The mixture was stirred for 30 minutes at -10° and filtered. Concentration of the filtrate left a yellow oil which was partially purified by absorption on a pad of silica gel (800 ml.) and elution with chloroform (ca 3000 ml.). Concentration of the eluates gave an oil (92.9 g., 100%) which was found to contain a minimum of 90% of the title ester as a mixture of epimers.

Workup

  1. temperatureTo a cooled (-10°)
  2. waitwas done over ca 15 minutes
  3. filtrationfiltered
  4. waitConcentration of the filtrate left a yellow oil which
  5. customwas partially purified by absorption on a pad of silica gel (800 ml.) and elution with chloroform (ca 3000 ml.)
  6. customConcentration of the eluates gave an oil (92.9 g., 100%) which
  7. additionas a mixture of epimers

Sources & evidence

ORD record
ord-fa7472b9ee8a4d98b1399393e9b65ff9
Source dataset
uspto-grants-1979_10
Patent number
US04169833

Reaction notes

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