Hydrochloric Acid → 7-Amino-3-(benzothiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1702049Notes

Reaction equation

HRID 1702049 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C(=O)(O)[O-].[Na+].Cl>O.CC(C)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[S:21][C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]=3)[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178418395HCID 178418395, compound

Product 1

HCID 128210677-Amino-3-(benzothiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acidYield 58.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of 7-aminocephalosporanic acid (23.1 g., purity 86.4%) and 2-mercaptobenzothiazole (14.7 g.) in water (800 ml.), sodium bicarbonate (13.5 g.) was added portionwise with stirring, and acetone (250 ml.) was added thereto. The mixture was stirred at 73° C. for 4.5 hours, cooled below 20° C. and adjusted to pH 3.4 with 6 N hydrochloric acid. The precipitating crystals were collected by filtration, washed with water and acetone in turn and dried under reduced pressure to give 7-amino-3-(benzothiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (18.7 g.).

Workup

  1. additionwas added portionwise
  2. stirringThe mixture was stirred at 73° C. for 4.5 hours
  3. temperaturecooled below 20° C.
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with water and acetone in turn
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-29a047ab606048f292bf5ff5c84ccd18
Source dataset
uspto-grants-1983_04
Patent number
US04379922

Reaction notes

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