2,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate

HRID 1660584Notes

Reaction equation

HRID 1660584 reaction equation
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[N:5]1[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:4]1[S:3]2>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[S:3][C@@H:4]2[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:16](=[O:28])[N:5]2[CH:6]([C:7]([O:9][CH2:10][C:11]([Cl:12])([Cl:13])[Cl:14])=[O:8])[CH:15]=1

Participants

4

Reactant 1

HCID 128339582,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 131803442,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylateYield 21.7%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Titanium tetrachloride (0.19 g.) was added to a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-(2-phenylacetamido)penam-3-carboxylate (0.46 g.) in dried dichloromethane (5 ml.) and the mixture was stirred for 2.5 hours. After the reaction, the reaction mixture was washed in turn with 2% hydrochloric acid three times, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate. After the solvent was distilled off the residue (0.43 g.) was purified by column chromatography on silica gel (10 g.) using chloroform as developing solvent to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate (0.1 g.) mp 136° to 137° C.

Workup

  1. customAfter the reaction
  2. washthe reaction mixture was washed in turn with 2% hydrochloric acid three times
  3. dry with materiala saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over magnesium sulfate
  4. distillationAfter the solvent was distilled off the residue (0.43 g.)
  5. customwas purified by column chromatography on silica gel (10 g.)

Sources & evidence

ORD record
ord-89f59891b185423ab63f7e38987f391f
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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