N,N-Diethylaniline → HCID 88690516, compound

HRID 1979912Notes

Reaction equation

HRID 1979912 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7]Br.[NH2:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:21])=[C:14]([CH2:17][O:18][CH3:19])[CH2:15][S:16][C@H:11]12.C(N(CC)C1C=CC=CC=1)C>C(Cl)Cl>[Br:7][CH2:6][C:2]([CH2:3][C:4]([NH:9][CH:10]1[C:31](=[O:32])[N:12]2[C:13]([C:20]([O:22][CH2:23][O:24][C:25](=[O:30])[C:26]([CH3:27])([CH3:28])[CH3:29])=[O:21])=[C:14]([CH2:17][O:18][CH3:19])[CH2:15][S:16][C@H:11]12)=[O:5])=[O:1]

Participants

6

Reactant 4

HCID 7061N,N-DiethylanilineHCID 12661DiketeneHCID 24408BromineHCID 67733429HCID 67733429, compound

Product 1

HCID 88690516HCID 88690516, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-30 °C

Procedure

168 mg of diketene were dissolved in 2 ml of methylene chloride and, whilst stirring the solution, it was cooled to -30° C. To the solution was then added dropwise a solution of 320 mg of bromine in 2 ml of methylene chloride, and the resulting mixture was added dropwise to a solution of 322 mg of pivaloyloxymethyl 7-amino-3-methoxymethyl-3-cephem-4-carboxylate and 299 mg of N,N-diethylaniline in 5 ml of methylene chloride, which had been cooled to -5° C. The mixture was left to stand for 30 minutes, after which it was concentrated by evaporation under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, washed, in turn, with 5 ml each of water, 5% w/v aqueous hydrochloric acid and a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulphate. The drying agent was filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue was chromatographed through a column containing 30 g of silica gel, eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to give 288 mg of the title compound.

Workup

  1. temperaturehad been cooled to -5° C
  2. waitThe mixture was left
  3. concentrationafter which it was concentrated by evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  5. washwashed, in turn, with 5 ml each of water, 5%
  6. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulphate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. customThe residue was chromatographed through a column
  10. additioncontaining 30 g of silica gel
  11. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-2c76cdfe21aa45e48b1a76ed81193561
Source dataset
uspto-grants-1984_11
Patent number
US04483855

Reaction notes

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