N,N-Diethylaniline → HCID 131713980, compound

HRID 1153782Notes

Reaction equation

HRID 1153782 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:12]([O:14][CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@H:3]12.C(N(CC)C1C=CC=CC=1)C.[Cl:36][CH2:37][C:38]([NH:40][C:41]1[S:42][CH:43]=[C:44]([C:46](=[N:50][O:51][CH3:52])[C:47](O)=[O:48])[N:45]=1)=[O:39]>C(Cl)Cl>[Cl:36][CH2:37][C:38]([NH:40][C:41]1[S:42][CH:43]=[C:44]([C:46](=[N:50][O:51][CH3:52])[C:47]([NH:1][CH:2]2[C:23](=[O:24])[N:4]3[C:5]([C:12]([O:14][CH2:15][O:16][C:17](=[O:22])[C:18]([CH3:19])([CH3:20])[CH3:21])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@H:3]23)=[O:48])[N:45]=1)=[O:39]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 581157C8H8ClN3O4SHCID 67733429HCID 67733429, compound

Product 1

HCID 131713980HCID 131713980, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Meanwhile, 121 mg of pivaloyloxymethyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate and 141 mg of N,N-diethylaniline were dissolved in 5 ml of methylene chloride and stirred at -5° C. The resulting mixture was added dropwise to the mixture containing 2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid prepared as described above. The reaction mixture was stirred for 15 minutes and then concentrated by evaporation under reduced pressure. To the residue were added 20 ml of ethyl acetate and 5 ml of water, and the ethyl acetate layer was separated, washed, in turn, with 5 ml of a saturated aqueous solution of sodium bicarbonate, 5 ml of a 5% w/v aqueous solution of hydrogen chloride and 5 ml of a saturated aqueous solution of sodium chloride, and finally dried over anhydrous magnesium sulphate. The drying agent was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through 10 g of silica gel eluted with a 2:1 by volume mixture of ethyl acetate and hexane, to afford 55 mg of pivaloyloxymethyl 7-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate.

Workup

  1. additionThe resulting mixture was added dropwise to the mixture
  2. customprepared
  3. stirringThe reaction mixture was stirred for 15 minutes
  4. concentrationconcentrated by evaporation under reduced pressure
  5. additionTo the residue were added 20 ml of ethyl acetate and 5 ml of water
  6. customthe ethyl acetate layer was separated
  7. washwashed, in turn, with 5 ml of a saturated aqueous solution of sodium bicarbonate, 5 ml of a 5% w/v aqueous solution of hydrogen chloride and 5 ml of a saturated aqueous solution of sodium chloride
  8. dry with materialfinally dried over anhydrous magnesium sulphate
  9. filtrationThe drying agent was filtered off
  10. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  11. washeluted with a 2:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-6889e2dabd9044a0812f8144c77e3684
Source dataset
uspto-grants-1984_12
Patent number
US04486425

Reaction notes

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