Dibutylamine → HCID 88606953, compound

HRID 1088653Notes

Reaction equation

HRID 1088653 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7]Br.[CH3:9][C:10]1[CH2:19][S:18][C@@H:13]2[C@H:14]([NH2:17])[C:15](=[O:16])[N:12]2[C:11]=1[C:20]([OH:22])=[O:21].CCCCNCCCC>C(Cl)Cl>[Br:7][CH2:6][C:2](=[O:1])[CH2:3][C:4]([NH:17][CH:14]1[C:15](=[O:16])[N:12]2[C:11]([C:20]([OH:22])=[O:21])=[C:10]([CH3:9])[CH2:19][S:18][C@H:13]12)=[O:5]

Participants

6

Reactant 4

HCID 8148DibutylamineHCID 12661DiketeneHCID 24408BromineHCID 334987-Aminodeacetoxycephalosporanic acid

Product 1

HCID 88606953HCID 88606953, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.2 g of diketene in 5 ml of methylene chloride was cooled to -40° C. and 4.4 g of bromine were added dropwise. Separately, 4.28 g of 7-aminodesacetoxycephalosporanic acid and 8.0 g of n-dibutylamine were dissolved in 120 ml of methylene chloride and cooled. The above reaction mixture was added dropwise to this mixed solution. The temperature of the mixture was increased to room temperature over 30 minutes, after which the mixture was stirred for an additional 30 minutes. The solvent was distilled off under reduced pressure and the resulting residue was shaken vigorously with 200 ml of ethyl acetate and 40 ml of 40% phosphoric acid. The orgnaic layer was taken, washed with water, dried and concentrated to dryness under reduced pressure. To the residue was added ethyl ether, followed by stirring. The resultant powder was collected by filtration and dried. By the above procedure there were obtained 3.7 g of the captioned compound.

Workup

  1. temperaturecooled
  2. customThe above reaction mixture
  3. additionwas added dropwise to this mixed solution
  4. distillationThe solvent was distilled off under reduced pressure
  5. stirringthe resulting residue was shaken vigorously with 200 ml of ethyl acetate and 40 ml of 40% phosphoric acid
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated to dryness under reduced pressure
  9. additionTo the residue was added ethyl ether
  10. stirringby stirring
  11. filtrationThe resultant powder was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-f89fd2d340ee4fdf8396de4b62c289b0
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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