Hydrochloric Acid → Cephalosporanic Acid

HRID 1836699Notes

Reaction equation

HRID 1836699 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10](N)[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].C(=O)(O)[O-].[K+].Cl>O.CC(O)C>[C:2]([O:4][CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516893Potassium Bicarbonate

Product 1

HCID 12302722Cephalosporanic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

Solutions A and B are produced according to a method as described in Example 2, but using in solution A 18.57 g of 7-aminocephalosporanic acid instead of 18.57 g of 7-amino-3-{[(2,5-dihydro-6-hydroxy-2-methyl-5-oxo-as-triazin-3-yl)thio]methyl}-3-cephem-4-carboxylic acid. While stirring the mixture obtained is poured onto an ice-cooled suspension of potassium bicarbonate in a mixture of water and 2-propanol. The pH of the two-phase system obtained is adjusted to 2.0 with 2 N HCl. The organic phase is separated off and treated with 7.5 ml of water and 3.81 g thiourea while stirring. The pH of the mixture is kept between 3.0 and 3.5 by addition of a solution of 2-amino-2,4,4-trimethylpentane in dichloromethane. A precipitate is obtained. 2-Propanol is added to the suspension obtained while stirring and the precipitate is isolated and dried. 7-[2-(Aminothiazol-4-yl)-2(Z)-methoximino)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid is obtained.

Workup

  1. customobtained
  2. temperaturecooled
  3. customThe pH of the two-phase system obtained
  4. customThe organic phase is separated off
  5. additiontreated with 7.5 ml of water and 3.81 g thiourea
  6. stirringwhile stirring
  7. additionThe pH of the mixture is kept between 3.0 and 3.5 by addition of a solution of 2-amino-2,4,4-trimethylpentane in dichloromethane
  8. customA precipitate is obtained
  9. customobtained
  10. stirringwhile stirring
  11. customthe precipitate is isolated
  12. customdried

Sources & evidence

ORD record
ord-2e621c042f504376bba7910c8fefb7d1
Source dataset
uspto-grants-2004_08
Patent number
US06777549B2

Reaction notes

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