HCID 70360981, compound → HCID 70592416, compound

HRID 1856168Notes

Reaction equation

HRID 1856168 reaction equation
[CH3:1][C:2]1[S:6][C:5]([SH:7])=[N:4][N:3]=1.Br[CH2:9][C:10]1([CH3:33])[CH:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]2[C:19](=[O:32])[CH:20]([NH:21][C:22](=[O:31])[CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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([CH3:33])[CH:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]3[C:19](=[O:32])[CH:20]([NH:21][C:22](=[O:31])[CH2:23][O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C@H:12]3[S:11]2)=[N:4][N:3]=1

Participants

5

Reactant 2

HCID 70360981HCID 70360981, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 70592416HCID 70592416, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 1061PhosphateSolvent

Procedure

5-Methyl-1,3,4-thiadiazole-2-thiol (0.4 g) was dissolved in a mixture of pH 7.3 phosphate buffer (20 ml) and acetone (20 ml). To this solution was added a solution of methyl 2-bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate (0.80 g) in acetone (10 ml) and the mixture was stirred for 4 hours at room temperature. After the reaction was completed, acetone was distilled off from the reaction mixture and the residue was extracted with ethyl acetate. The extract 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 subjected to column chromatography on silica gel (60 g) and eluted with chloroform. The eluate was separated into fractions of each about 30 ml to give methyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylate (0.28 g) from the fourth to seventh fractions.

Workup

  1. distillationacetone was distilled off from the reaction mixture
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with sodium bicarbonate aqueous solution
  4. dry with materialwith water and thereafter dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. washeluted with chloroform
  7. customThe eluate was separated into fractions of each about 30 ml

Sources & evidence

ORD record
ord-b5b90b0e74964efbb933a98fa5a1a388
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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