Thionyl Chloride → Methyl 7-phthalimido-3-methylenecepham-4-carboxylate 1-oxide

HRID 972227Notes

Reaction equation

HRID 972227 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].S(Cl)(Cl)=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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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

Procedure

The same procedure was followed as in Example 1 (I) above except 0.20 g. of methyl 3-methyl-2-(2-sulfino-4-oxo-3-phthalimido-1-azetidinyl)-3-butenoate was employed as the starting material instead of the sulfinyl chloride. The reaction provided 0.10 g. of the title compound.

Workup

  1. customThe reaction provided 0.10 g

Sources & evidence

ORD record
ord-a562cd70441b4a0a895e820c7807393f
Source dataset
uspto-grants-1977_10
Patent number
US04052387

Reaction notes

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