Sodium Hydroxide → HCID 178460996, compound

HRID 1833534Notes

Reaction equation

HRID 1833534 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][NH:12][C:13]([NH2:15])=[O:14])[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][NH:12][C:13]([NH2:15])=[O:14])[CH2:7][S:8][C@H:3]12)=[S:35]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 21249692Methylthioacetyl chlorideHCID 178514095HCID 178514095, compound

Product 1

HCID 178460996HCID 178460996, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred, cooled (-20°) solution of 10.4 g. (0.026 mol.) of 7-amino-3-[1-(2-ureidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 220 ml. of 3% sodium bicarbonate and 220 ml. of acetone is added dropwise 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 if acidified with 3N 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 10.4 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-9d4d4ded33624b638d565ecad3468a7e
Source dataset
uspto-grants-1978_01
Patent number
US04066761

Reaction notes

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