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Sodium Hydroxide → HCID 178460997, compound

HRID 2071828
Notes
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Reaction equation

HRID 2071828 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 180
Acetone
Solvent
2×

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 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 10.8 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-996ef95e59884f0e9ee14f3531f34e3c
Source dataset
uspto-grants-1977_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04048311

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes