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

HRID 2083141Notes

Reaction equation

HRID 2083141 reaction equation
[CH3:1][C:2]1[S:6][C:5]([SH:7])=[N:4][N:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:14][C:15]1([CH3:41])[CH:19]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[N:18]2[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:17]2[S:16]1.O>C(N)=O>[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:14][C:15]2([CH3:41])[CH:19]([C:20]([O:22][CH2:23][C:24]([Cl:25])([Cl:26])[Cl:27])=[O:21])[N:18]3[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C@H:17]3[S:16]2)=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 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 33.8%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

5-Methyl-1,3,4-thiadiazole-2-thiol (0.20 g) and sodium bicarbonate (0.85 g) were dissolved in formamide (7 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 5 hours at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate aqueous solution and then with water and thereafter dried over magnesium sulfate. The residue obtained by distilling off the solvent 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 (0.20 g) from the third fraction of fractions each of which was separated into about 30 ml.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate aqueous solution
  3. dry with materialwith water and thereafter dried over magnesium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f1b5cbbe98034cf58134d55f87521dae
Source dataset
uspto-grants-1978_04
Patent number
US04084049

Reaction notes

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