HCID 54307869, compound → HCID 21292928, compound

HRID 972230Notes

Reaction equation

HRID 972230 reaction equation
N1(S([Br:8])=O)CCC1=O.[C:9]1(=[O:34])[N:13]([CH:14]2[C:27](=[O:28])[N:16]3[CH:17]([C:23]([O:25][CH3:26])=[O:24])[C:18](=[CH2:22])[CH2:19][S:20](=[O:21])[C@H:15]23)[C:12](=[O:29])[C:11]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:10]12>C(Cl)Cl>[CH3:19][C:18](=[CH2:22])[CH:17]([N:16]1[C:27](=[O:28])[CH:14]([N:13]2[C:12](=[O:29])[C:11]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:10]3[C:9]2=[O:34])[CH:15]1[S:20]([Br:8])=[O:21])[C:23]([O:25][CH3:26])=[O:24]

Participants

4

Reactant 2

HCID 54307869HCID 54307869, compoundHCID 69799987Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

Product 1

HCID 21292928HCID 21292928, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The azetidinone sulfinyl bromide from above was dissolved in 20 ml. of methylene chloride; 0.6 ml. of stannic chloride was added to the solution. After 45 minutes at room temperature the reaction mixture was washed with water and brine, dried over anhydrous MgSO4, and evaporated in vacuo to dryness to provide 1.15 g. of methyl 7-phthalimido-3-methylenecepham-4-carboxylate-1-oxide (a mixture of R- and S-sulfoxide isomers). For the predominant isomer: nmr (CDCl3) δ3.64, 4.20 (ABq, 2, J=13.0 Hz, C2 --H), 3.84 (s, 3, COOCH3), 4.90 (d, 1, J=4.0 Hz, β-lactam H), 5.3-5.7 (m, 3), 5.97 (d, 1, J=4.0 Hz, β-lactam H), and 7.84 (bs, 4, ArH).

Workup

  1. washAfter 45 minutes at room temperature the reaction mixture was washed with water and brine
  2. dry with materialdried over anhydrous MgSO4
  3. customevaporated in vacuo to dryness
  4. customto provide 1.15 g

Sources & evidence

ORD record
ord-3ad909f33c7a470d902e731f28031665
Source dataset
uspto-grants-1977_10
Patent number
US04052387

Reaction notes

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