Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate → Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

HRID 236923Notes

Reaction equation

HRID 236923 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](Cl)=[O:25])[C:4]([O:6][CH3:7])=[O:5]>C(OCC)(=O)C>[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](=[CH2:27])[CH2:1][S:24](=[O:25])[C@H:9]23)[C:14](=[O:23])[C:15]2=[CH:22][CH:21]=[CH:20][CH:19]=[C:16]12

Participants

3

Reactant 1

HCID 20394803Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate

Product 1

HCID 69799987Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxideYield 27.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate (0.20 g.) was stirred in about 27 g. of polyphosphoric acid for 20 minutes. Ice water and ethyl acetate (25 ml.) was added to the reaction mixture. The organic layer was separated and washed successively with water, aqueous sodium bicarbonate, and brine, dried (MgSO4), and evaporated in vacuo to dryness to give methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide (0.05 g.) as a white foam.

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water, aqueous sodium bicarbonate, and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-b352b7b7d7d5408ab0d80bc4cbdb0f07
Source dataset
uspto-grants-1979_06
Patent number
US04159266

Reaction notes

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