Water → HCID 70593095, compound

HRID 2083146Notes

Reaction equation

HRID 2083146 reaction equation
Br[CH2:2][C:3]1([CH3:38])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[CH2:20][N:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:22]([O:24][CH:25]([CH:27]3[CH2:29][CH2:28]3)[CH3:26])=[O:23])[C@H:5]2[S:4]1.C(=O)(O)[O-].[Na+].[CH3:44][C:45]1[S:49][C:48]([SH:50])=[N:47][N:46]=1.O>C(N)=O>[CH3:44][C:45]1[S:49][C:48]([S:50][CH2:2][C:3]2([CH3:38])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]3[C:16](=[O:37])[CH:17]([NH:18][C:19](=[O:36])[CH2:20][N:21]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:22]([O:24][CH:25]([CH:27]4[CH2:29][CH2:28]4)[CH3:26])=[O:23])[C@H:5]3[S:4]2)=[N:47][N:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 70590774HCID 70590774, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 70593095HCID 70593095, compoundYield 10.8%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent2×

Procedure

A solution of 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate (3.6 g) in formamide (40 ml) was added to a solution of sodium bicarbonate (0.66 g) and 5-methyl-1,3,4-thiadiazole-2-thiol (1.1 g) in formamide (60 ml) under ice-cooling, after which the mixture was stirred for 4.5 hours at the same temperature. After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with 5% sodium bicarbonate aqueous solution and then with water, dried, after which the solvent was distilled off. The oily residue was subjected to column chromatography on silica gel (110 g) and eluted with chloroform. The eluate was separated into fractions of each 50 ml and after collecting the fractions of the fifteenth and sixteenth, the solvent was distilled off to give oily 2,2,2-trichloroethyl 2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-2-methyl-6-[N-(1-cyclopropylethoxy)carbonylphenylglycyl]aminopenam-3-carboxylate (0.42 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 5% sodium bicarbonate aqueous solution
  4. dry with materialwith water, dried
  5. distillationafter which the solvent was distilled off
  6. washeluted with chloroform
  7. customThe eluate was separated into fractions of each 50 ml
  8. customafter collecting the fractions of the fifteenth and sixteenth, the solvent
  9. distillationwas distilled off

Sources & evidence

ORD record
ord-b8ee0bc5872742db8cd0ede8d75b2d3c
Source dataset
uspto-grants-1978_04
Patent number
US04084049

Reaction notes

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