Methanesulfonic Acid → 7beta-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid

HRID 483028Notes

Reaction equation

HRID 483028 reaction equation
CS(O)(=O)=O.CC(O[CH2:10][C:11]1[CH2:20][S:19][C@@H:14]2[C@H:15]([NH2:18])[C:16](=[O:17])[N:13]2[C:12]=1[C:21]([OH:23])=[O:22])=O.[C:24]([NH:27][N:28]1[C:32]([SH:33])=[N:31][N:30]=[N:29]1)(=[O:26])[CH3:25].[OH-].[NH4+]>C(#N)C.O>[NH2:18][C@@H:15]1[C:16](=[O:17])[N:13]2[C:12]([C:21]([OH:23])=[O:22])=[C:11]([CH2:10][S:33][C:32]3[N:28]([NH:27][C:24](=[O:26])[CH3:25])[N:29]=[N:30][N:31]=3)[CH2:20][S:19][C@H:14]12

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14923Ammonium HydroxideHCID 4413287-Aminocephalosporanic acidHCID 178475130HCID 178475130, compound

Product 1

HCID 704535287beta-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acidYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Methanesulfonic acid (5.77 g, 60 mmol) was added dropwise to a solution of 7β-aminocephalosporanic acid (3.27 g, 12.0 mmol) and 1-acetamido-5-mercapto-1H-tetrazole (2.50 g, 15.7 mmol) in acetonitrile (15 ml). The mixture was stirred at room temperature for 30 minutes and at 50° C. for 4 hours. Water (20 ml) was added with cooling to the reaction mixture, which was then adjusted to pH 3.5 with 28% aqueous ammonium hydroxide. Precipitates formed were filtered, washed with water and acetone successively and dried to give pale brown powder of 7β-amino-3-[(1-acetamido-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (3.36 g, 75. 3%), mp~195° C. (decomposition).

Workup

  1. temperaturewith cooling to the reaction mixture, which
  2. customPrecipitates
  3. customformed
  4. filtrationwere filtered
  5. washwashed with water and acetone successively
  6. customdried

Sources & evidence

ORD record
ord-11119a67e57b42ec8ac5c67b25957fae
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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