Sodium Chloride → HCID 131715625, compound

HRID 845132Notes

Reaction equation

HRID 845132 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+].[C:36](=[O:49])([O:41][CH:42]([CH:46]([CH3:48])[CH3:47])[CH:43]([CH3:45])[CH3:44])[O:37][CH:38](I)[CH3:39].C(OCC)(=O)C.[Cl-].[Na+]>CN(C)C=O>[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:38]([O:37][C:36]([O:41][CH:42]([CH:43]([CH3:44])[CH3:45])[CH:46]([CH3:48])[CH3:47])=[O:49])[CH3:39])=[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 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 23679375HCID 23679375, compoundHCID 53758459HCID 53758459, compound

Product 1

HCID 131715625HCID 131715625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.78 g of 1-chloroethyl 2,4-dimethyl-3-pentyl carbonate and 5 g of sodium iodide is stirred in 30 ml of acetonitrile at 70° C. for 4 hours and concentrated. The residue is extracted with ether and concentrated to give crude 1-iodoethyl 2,4-dimethyl-3-pentyl carbonate. In 30 ml of dimethylformamide is dissolved 3.6 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 with ice-cooling and stirring, the above 1-iodoethyl 2,4-dimethyl-3-pentyl carbonate is added thereto at one stroke, followed by stirring for 5 minutes. The reaction mixture is poured into a mixture of 150 ml of ethyl acetate and 150 ml of ice-cooled 20% aqueous sodium chloride. The organic layer is separated, washed with two 150-ml portions of saturated aqueous sodium chloride and extracted with 40 ml of 1N hydrochloric acid. The extract is subjected to column chromatography using Diaion MCI® GEL CHP-20P (Mitsubishi Chemical Industries Limited, Japan), elution being carried out with acetonitrile-0.01N hydrochloric acid. The fractions containing the desired product are combined and lyophilized to give 940 mg of the title compound as a white powder.

Workup

  1. temperaturewith ice-cooling
  2. stirringby stirring for 5 minutes
  3. customThe organic layer is separated
  4. washwashed with two 150-ml portions of saturated aqueous sodium chloride
  5. extractionextracted with 40 ml of 1N hydrochloric acid
  6. washDiaion MCI® GEL CHP-20P (Mitsubishi Chemical Industries Limited, Japan), elution
  7. additionThe fractions containing the desired product

Sources & evidence

ORD record
ord-a609f1d4b7a14ab795eb27eaa0e3128e
Source dataset
uspto-grants-1988_07
Patent number
US04755598

Reaction notes

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