Sodium Hydroxide → HCID 178460997, compound

HRID 237158Notes

Reaction equation

HRID 237158 reaction equation
[NH2:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH:9]([S:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)[CH2:10][CH2:11][S:12](=[O:15])(=[O:14])[NH2:13])[CH2:7][S:8][C@H:3]12.C(=O)(O)[O-].[Na+].[CH3:32][CH2:33][C:34](Cl)=[S:35].[OH-].[Na+]>CC(C)=O>[CH3:32][CH2:33][C:34]([NH:1][CH:2]1[C:25](=[O:26])[N:4]2[C:5]([C:22]([OH:24])=[O:23])=[C:6]([CH:9]([S:16][C:17]3[NH:18][N:19]=[N:20][N:21]=3)[CH2:10][CH2:11][S:12](=[O:14])(=[O:15])[NH2:13])[CH2:7][S:8][C@H:3]12)=[S:35]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 21249692Methylthioacetyl chlorideHCID 178508099HCID 178508099, compound

Product 1

HCID 178460997HCID 178460997, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred, cooled (-20°) solution of 10.8 g. (0.026 mol.) of 7-amino-3-[1-(2-sulfamoylethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 220 ml. of 3% sodium bicarbonate and 220 ml. of acetone is dropwise added a solution of 3.66 g. (0.029 mol.) of methylthioacetyl chloride in 52 ml. of acetone, during which time the pH of the reaction mixture is maintained at 8.0 by addition of 10% sodium hydroxide. After addition the reaction mixture is stirred an additional 20 minutes at -15°, then is warmed to 25° and extracted with ether. The remaining aqueous phase is cooled, 250 ml. of ethyl acetate is added and the slurry is acidified with 3 N hydrochloric acid. The layers are separated and the aqueous phase is extracted twice more with ethyl acetate. The combined extracts are dried (MgSO4) and evaporated to dryness to yield the title compound.

Workup

  1. temperatureTo a stirred, cooled (-20°) solution of 10.8 g
  2. additionAfter addition the reaction mixture
  3. temperatureis warmed to 25°
  4. extractionextracted with ether
  5. temperatureThe remaining aqueous phase is cooled
  6. additionof ethyl acetate is added
  7. customThe layers are separated
  8. extractionthe aqueous phase is extracted twice more with ethyl acetate
  9. dry with materialThe combined extracts are dried (MgSO4)
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-54908d6741184918918addd23e44f83b
Source dataset
uspto-grants-1979_06
Patent number
US04159373

Reaction notes

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