Sodium Hydroxide → HCID 178460998, compound

HRID 866882Notes

Reaction equation

HRID 866882 reaction equation
[NH2:1][CH:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([CH:9]([S:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)[CH2:10][CH2:11][NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:7][S:8][C@H:3]12.[CH3:28][CH2:29][C:30](Cl)=[S:31].[OH-].[Na+]>C(=O)(O)[O-].[Na+].CC(C)=O>[CH3:28][CH2:29][C:30]([NH:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([CH:9]([S:17][C:18]3[NH:19][N:20]=[N:21][N:22]=3)[CH2:10][CH2:11][NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:7][S:8][C@H:3]12)=[S:31]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21249692Methylthioacetyl chlorideHCID 178505107HCID 178505107, compound

Product 1

HCID 178460998HCID 178460998, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred, cooled (-20°) solution of 11.32 g (0.026 mol) of 7-amino-3-[1-(2-methanesulfonamidoethyl)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 is 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. additionAfter addition the reaction mixture
  2. temperatureis warmed to 25°
  3. extractionextracted with ether
  4. temperatureThe remaining aqueous phase is cooled
  5. addition250 ml of ethyl acetate is added
  6. customThe layers are separated
  7. extractionthe aqueous phase is extracted twice more with ethyl acetate
  8. dry with materialThe combined extracts are dried (MgSO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-609d0bb0292443f48be2fc9da85900b9
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Reaction notes

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