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

HRID 1856165Notes

Reaction equation

HRID 1856165 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 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 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-ea45b2949df3438e8f644c05afaaf5c1
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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