2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate → 2,2,2-Trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate

HRID 1856164Notes

Reaction equation

HRID 1856164 reaction equation
[CH3:1][C:2]1[S:6][C:5]([SH:7])=[N:4][N:3]=1.Br[CH2:9][C:10]1([CH3:36])[CH:14]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])[N:13]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:12]2[S:11]1>P([O-])([O-])([O-])=O.CC(C)=O>[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:9][C:10]2([CH3:36])[CH:14]([C:15]([O:17][CH2:18][C:19]([Cl:20])([Cl:21])[Cl:22])=[O:16])[N:13]3[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@H:12]3[S:11]2)=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylateHCID 178434161HCID 178434161, compound

Product 1

HCID 705902602,2,2-Trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylateYield 15.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1061PhosphateSolvent

Procedure

5-Methyl-1,3,4-thiadiazole-2-thiol (0.16 g) was dissolved in a mixture of pH 6.5 phosphate buffer (5 ml) and acetone (10 ml). To this solution was added 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g) and the mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduced pressure and acetone was distilled off and thereafter the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with sodium bicarbonate aqueous solution and then with water and thereafter dried over magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography on silica gel using chloroform as developing solvent to give oily 2,2,2-trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-(2-phenylacetamido)-penam-3-carboxylate (0.09 g) from the second and third fractions each of which was separated into about 30 ml.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and acetone
  2. distillationwas distilled off
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with sodium bicarbonate aqueous solution
  5. dry with materialwith water and thereafter dried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4edffc9adb2c41d5836b0e7d21845f83
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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