1,2-Dichloroethane → Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

HRID 972225Notes

Reaction equation

HRID 972225 reaction equation
[CH3:1][C:2](=[CH2:27])[CH:3]([N:8]1[C:11](=[O:12])[CH:10]([N:13]2[C:17](=[O:18])[C:16]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]3[C:14]2=[O:23])[CH:9]1[S:24]([OH:26])=O)[C:4]([O:6][CH3:7])=[O:5].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.ClCCCl.C(OCC)(=O)C>[Cl-].[Na+].O>[C:17]1(=[O:18])[N:13]([CH:10]2[C:11](=[O:12])[N:8]3[CH:3]([C:4]([O:6][CH3:7])=[O:5])[C:2](=[CH2:1])[CH2:27][S:24](=[O:26])[C@H:9]23)[C:14](=[O:23])[C:15]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]12

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 14812Phosphorus oxide (P4O10)HCID 21314440Methyl 3-methyl-2-(2-sulfino-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

Product 1

HCID 69799987Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 0.10 g. of methyl 3-methyl-2-(2-sulfino-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate and 0.04 g. of phosphorous pentoxide in 20 ml. of 1,2-dichloroethane was stirred at room temperature for 1 hour. A tlc of the reaction mixture indicated only trace amounts of the methylenecepham sulfoxide. The mixture was then refluxed for 30 minutes, cooled to room temperature, and combined with 25 ml. of ethyl acetate and 50 ml. of brine. The organic layer was separated, washed with aqueous sodium bicarbonate and brine and dried (MgSO4). Evaporation in vacuo to dryness provided 0.04 g. of the title product as a white froth.

Workup

  1. temperatureThe mixture was then refluxed for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation in vacuo to dryness
  6. customprovided 0.04 g

Sources & evidence

ORD record
ord-f78088c1afc74d1cbe3c508151233b4d
Source dataset
uspto-grants-1977_10
Patent number
US04052387

Reaction notes

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