Hydrochloric Acid → HCID 15593467, compound

HRID 2291596Notes

Reaction equation

HRID 2291596 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O-:32])=[O:31])=[C:15]([CH2:18][S:19][C:20]4[N:24]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[N:23]=[N:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[K+].[CH:36]1([C:42]([O:44][CH:45](I)[CH:46]([CH3:48])[CH3:47])=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.CCOCC.[ClH:55]>CC(N(C)C)=O>[ClH:55].[ClH:55].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:33](=[O:34])[N:13]3[C:14]([C:30]([O:32][CH:45]([O:44][C:42]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[O:43])[CH:46]([CH3:48])[CH3:47])=[O:31])=[C:15]([CH2:18][S:19][C:20]4[N:24]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[N:23]=[N:22][N:21]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 15593465HCID 15593465, compoundHCID 23679375HCID 23679375, compound

Product 1

HCID 15593467HCID 15593467, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

In 120 ml of dimethylacetamide is dissolved 6.0 g of potassium 7β[2-(2-aminothiazol-4-yl) acetamido]-3-[[[1-(2-dimethylaminoethyl) -1H-tetrazol-5-yl]thio]-methyl]ceph-3-em-4-carboxylate and the solution is cooled to 0° C. With stirring, 9.0 g of 1-iodo-2-methylpropyl cyclohexanecarboxylate is added at one stroke to the solution, followed by stirring for further 10 minutes. To the reaction mixture is added 70 ml of 2 N HCl-ether, followed by addition of 300 ml of ether. The ether layer is discarded and the residue is dissolved in 50 ml of 1 N hydrochloric acid and subjected to column chromatography on XAD-II ®resin (Rohm & Haas Co. U.S.A.), elution being carried out with water-acetonitrile (3:1). The fractions containing the desired product are combined, evaporated under reduced pressure to remove the solvent and lyophilized to give 2.5 g of the title compound as a colorless powder.

Workup

  1. stirringby stirring for further 10 minutes
  2. washsubjected to column chromatography on XAD-II ®resin (Rohm & Haas Co. U.S.A.), elution
  3. additionThe fractions containing the desired product
  4. customevaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-4b3188966e914a37866a9172fa10b751
Source dataset
uspto-grants-1989_01
Patent number
US04797395

Reaction notes

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