Hydrochloric Acid → HCID 88600928, compound

HRID 1979619Notes

Reaction equation

HRID 1979619 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7](=[S:9])[OH:8])[O:4][N:3]=1.C1CCN2C(=NCCC2)CC1.N1C=CC=C(C)C=1.CC(O[CH2:32][C:33]1[CH2:42][S:41][C@@H:36]2[C@H:37]([NH2:40])[C:38](=[O:39])[N:35]2[C:34]=1[C:43]([OH:45])=[O:44])=O.Cl>C(O)(C)C.O>[NH2:40][CH:37]1[C:38](=[O:39])[N:35]2[C:34]([C:43]([OH:45])=[O:44])=[C:33]([CH2:32][S:9][C:7]([C:5]3[O:4][N:3]=[C:2]([CH3:1])[CH:6]=3)=[O:8])[CH2:42][S:41][C@H:36]12

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79703-MethylpyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4413287-Aminocephalosporanic acidHCID 178427269HCID 178427269, compound

Product 1

HCID 88600928HCID 88600928, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

4.29 g (3 cmole) of 3-methylisoxazole-5-thiocarboxylic acid were dissolved in 300 ml of 60% isopropanol-water and there were added 1.6 ml of DBU (Example 9) and 3 ml of beta-picoline. At 65° C., there were added in one shot 3.0 g of 7-aminocephalosporanic acid, 90%. The mixture was stirred for 90 minutes and the reaction isoelectric pH was held to 5.5. The precipitate which formed was isolated after adjusting the pH to 4.0 at 25° C. by concentrated hydrochloric acid. The precipitate was filtered, washed with water and acetone to give 3.0 g of the compound of the title, with an 80% yield. The infrared and proton magnetic resonance spectra are consistent with its structure.

Workup

  1. additionAt 65° C., there were added in one
  2. customThe precipitate which formed
  3. customwas isolated
  4. customat 25° C.
  5. filtrationThe precipitate was filtered
  6. washwashed with water and acetone

Sources & evidence

ORD record
ord-cc859309d5604db3ab70ca80d59faac0
Source dataset
uspto-grants-1984_11
Patent number
US04481357

Reaction notes

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