Methane → HCID 70509628, compound

HRID 1730865Notes

Reaction equation

HRID 1730865 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.[S:19]1[CH2:23][CH2:22][N:21]=[C:20]1[SH:24].P([O-])([O-])([O-])=O.C([O-])(O)=O.[Na+].C.Cl>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:24][C:20]3[S:19][CH2:23][CH2:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

8

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178527880HCID 178527880, compound

Product 1

HCID 70509628HCID 70509628, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

7-ACA (13.65 g) and 2-thiazoline-2-thiol (11.92 g) are suspended in 500 ml. of phosphate buffer 0.2 M (Na2HPO4 /NaH2PO4) pH 6.5. To the suspension are added with stirring 12.6 g. of NaHCO3 and 250 ml. of acetone. The reaction medium is heated for 21/4 hrs with stirring on a 80° C water bath. The solution is then treated with charcoal, cooled (5°-10° C) and acidified to pH 4 with 2 N hydrochloric acid. The obtained suspension is diluted with acetone and stirred for 15-20 minutes. The precipitate is filtered, washed with water, acetone and ethyl ether and dried under reduced pressure to yield 7-amino-3-(2-thiazolin-2-ylthiomethyl)-3-cephem-4-carboxylic acid.

Workup

  1. additionTo the suspension are added
  2. temperatureThe reaction medium is heated for 21/4 hrs
  3. stirringwith stirring on a 80° C water bath
  4. temperaturecooled (5°-10° C)
  5. stirringstirred for 15-20 minutes
  6. filtrationThe precipitate is filtered
  7. washwashed with water, acetone and ethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-f1b8f268261b4b3aa66f49988019b86b
Source dataset
uspto-grants-1976_11
Patent number
US03994886

Reaction notes

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