Trifluoroacetic acid → Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

HRID 236924Notes

Reaction equation

HRID 236924 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].FC(F)(F)C(O)=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](=[CH2:27])[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 2

HCID 6422Trifluoroacetic acidHCID 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-oxide

Procedure

A solution of 0.29 g. of methyl 3-methyl-2-(2-chlorosulfinyl-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate in 10 ml. of trifluoroacetic acid was refluxed for 30 minutes and then was evaporated in vacuo to dryness. The product was dissolved in 20 ml. of ethyl acetate. The resulting solution was washed successively with aqueous sodium bicarbonate (3X), water, and brine, dried (MgSO4), and evaporated in vacuo to dryness to provide methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide.

Workup

  1. customwas evaporated in vacuo to dryness
  2. dissolutionThe product was dissolved in 20 ml
  3. washThe resulting solution was washed successively with aqueous sodium bicarbonate (3X), water, and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-78977b0b999041708180f64c2c6afc59
Source dataset
uspto-grants-1979_06
Patent number
US04159266

Reaction notes

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