7-Aminocephalosporanic acid → HCID 67661638, compound

HRID 1277810Notes

Reaction equation

HRID 1277810 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:3].[NH2:19][C:20]1[CH:25]=[C:24]([NH2:26])[N:23]=[C:22]([SH:27])[N:21]=1>O.C(=O)(O)[O-].[Na+]>[OH2:3].[OH2:3].[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:27][C:22]3[N:23]=[C:24]([NH2:26])[CH:25]=[C:20]([NH2:19])[N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 2

HCID 4413287-Aminocephalosporanic acidHCID 1785079174,6-diaminopyrimidine-2-thiol

Product 1

HCID 67661638HCID 67661638, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent2×

Conditions

Temperature
60 °C

Procedure

2.7 g (0.01 mole) of 7-aminocephalosporanic acid are dissolved in 50 ml of water with the required amount of sodium bicarbonate. 1.7 g (0.013 mole) of 4,6-diamino-2-mercaptopyrimidine and the equivalent amount of sodium bicarbonate are added and the reaction solution is heated to 60° C. for 4 hours, whilst stirring and keeping the pH value constant (pH=7). The mixture is allowed to cool, undissolved material is filtered off and the filtrate is concentrated in vacuo at 30° C. to half its volume. The aqueous solution which remains is extracted several times with ethyl acetate and the aqueous phase is adjusted to a pH of 2 with 2 N hydrochloric acid. The precipitate is filtered off, washed with water until free from chloride and dried in vacuo at 37° C. over potassium hydroxide. 1.61 g of the title compound are obtained. Rf : 0.27 (acetone:glacial acetic acid =10:1) IR (KBr): 1,745 cm-1 (β-lactam band) NMR (d6 -DMSO, 60 MHz):

Workup

  1. temperatureto cool
  2. filtrationundissolved material is filtered off
  3. concentrationthe filtrate is concentrated in vacuo at 30° C. to half its volume
  4. extractionThe aqueous solution which remains is extracted several times with ethyl acetate
  5. filtrationThe precipitate is filtered off
  6. washwashed with water until free from chloride
  7. dry with materialdried in vacuo at 37° C. over potassium hydroxide

Sources & evidence

ORD record
ord-1f716ead5e51485198b38dcbe2085798
Source dataset
uspto-grants-1981_07
Patent number
US04278793

Reaction notes

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