Acetone → HCID 12834187, compound

HRID 1660628Notes

Reaction equation

HRID 1660628 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:24])[CH:12]([NH:13][C:14](=[O:23])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[NH2:16])[C@H:4]2[S:3]1.[OH-].[Na+].[CH3:27][C:28]([CH3:30])=O>O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:24])[CH:12]([N:13]3[C:14](=[O:23])[CH:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:16][C:28]3([CH3:30])[CH3:27])[C@H:4]2[S:3]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 12834118HCID 12834118, compound

Product 1

HCID 12834187HCID 12834187, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-methyl-7-(2-phenylglycyl)amino-3-cephem-4-carboxylic acid (1.0 g) in water (10 ml) was adjusted to pH 8.8 by adding dropwise 10% sodium hydroxide. To the suspension was added acetone (10 ml), and the mixture was stirred for 24 hours in an ice bath. Acetone was removed under reduced pressure, and then the aqueous layer was adjusted to about pH 3.5 with 10% hydrochloric acid, and then extracted three times with ethyl acetate (20 ml). The residue obtained by distilling off ethyl acetate was dissolved in a small amount of acetone, and then a small quantity of insoluble material was filtrated off. A great quantity of ether was added to the filtrate, and then the precipitate was collected by filtration to give 2-methyl-7-(2,2-dimethyl-4-phenyl-5-oxoimidazolidin-1-yl)-3-cephem-4-carboxylic acid (0.30 g), mp 160° to 162° C. (dec.).

Workup

  1. customAcetone was removed under reduced pressure
  2. extractionextracted three times with ethyl acetate (20 ml)
  3. customThe residue obtained
  4. distillationby distilling off ethyl acetate
  5. dissolutionwas dissolved in a small amount of acetone
  6. filtrationa small quantity of insoluble material was filtrated off
  7. additionA great quantity of ether was added to the filtrate
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b9168235a9d94187b05a40adb65fe305
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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