Sodium Bicarbonate → HCID 131713625, compound

HRID 1463159Notes

Reaction equation

HRID 1463159 reaction equation
C(=O)(O)[O-].[Na+].C(O[CH2:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:21]([NH2:22])[C:20](=[O:23])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])(=O)C.[CH3:24][C:25]1[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([SH:32])[N:26]=1>O.CC(C)=O>[NH2:22][CH:21]1[C:20](=[O:23])[N:15]2[C:16]([C:17]([OH:19])=[O:18])=[C:11]([CH2:10][S:32][C:27]3[N:28]=[C:29]([CH3:31])[CH:30]=[C:25]([CH3:24])[N:26]=3)[CH2:12][S:13][C@H:14]12

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acidHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 131713625HCID 131713625, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent3×

Procedure

A solution of sodium bicarbonate (9.45 g.) in water (100 ml.) was added in portions to a stirred suspension of 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid (13.5 g.) in water (100 ml.) and acetone (50 ml.). The solid dissolved with effervescence. To this solution under nitrogen at 55° was added rapidly, drop by drop, a solution of 4,6-dimethyl-2-mercaptopyrimidine (10.5 g.) in water (100 ml.) and acetone (100 ml.), the pH being maintained between 7.4 and 7.8 by addition of 6 NHCl or 5% w/v aqueous NaHCO3. After 23 hours at 55°, the reaction mixture was cooled to 0° and acidified to pH 4.0. The resulting precipitate was filtered, washed with water and acetone, and dried over P2O5 to give 7-amino-3-(4,6-dimethylpyrimid-2-yl)thiomethylceph-3-em-4-carboxylic acid. A mixture of this acid (3.52 g.) and O-t-butyl-1,3-diisopropylisourea (6.0 g.) in dry CH2Cl2 (60 ml.) was stirred under nitrogen for 20 hours. The reaction mixture was filtered, the filtrate evaporated and the residue purified by chromatography on silica gel (200 g.) at -40° using CH2Cl2 /ether 6:4 v/v as eluant to give the t-butyl ester.

Workup

  1. dissolutionThe solid dissolved with effervescence
  2. additionTo this solution under nitrogen at 55° was added rapidly
  3. temperaturethe reaction mixture was cooled to 0°
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water and acetone
  6. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-c8779309aab5458d972e0f92aeb8303e
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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