Ethyl Acetate → HCID 13387255, compound

HRID 845130Notes

Reaction equation

HRID 845130 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:47])([O:41][CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45])[O:37][CH:38](I)[CH3:39].C(OCC)(=O)C>CC(N(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][CH2:42][CH:43]([CH3:46])[CH2:44][CH3:45])=[O:47])[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14157119HCID 14157119, compoundHCID 23679375HCID 23679375, compound

Product 1

HCID 13387255HCID 13387255, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-5 °C

Procedure

In 80 ml of dimethylacetamide is dissolved 5.6 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 the solution is cooled to -5° C. With stirring, 4.8 g of 1-iodoethyl 2-methylbutyl carbonate is added at one stroke and stirring is continued for 5 minutes. The reaction mixture is poured into a mixture of 300 ml of ethyl acetate and 200 ml of ice-water and the organic layer is separated. The aqueous layer is extracted with 200 ml of ethyl acetate and these organic layers are combined, water with three 150-ml portions of ice water and three 150-ml portions of saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate. The solvent is then distilled off and isopropyl ether is added to the residue. The thus-obtained white powder is collected by filtration, washed with isopropyl ether and dried to give 2.1 g of the title compound.

Workup

  1. stirringstirring
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted with 200 ml of ethyl acetate
  4. dry with materialwater with three 150-ml portions of ice water and three 150-ml portions of saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate
  5. distillationThe solvent is then distilled off
  6. additionisopropyl ether is added to the residue
  7. filtrationThe thus-obtained white powder is collected by filtration
  8. washwashed with isopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-495e2f1c4cec4e39ba7e1ae312f6a3f2
Source dataset
uspto-grants-1988_07
Patent number
US04755598

Reaction notes

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