1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 14459722, compound

HRID 2372710Notes

Reaction equation

HRID 2372710 reaction equation
[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[C:5]([C:12]([O-:14])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@H:3]12.N12CCCN=C1CCCCC2.[CH3:28][C:29]([CH3:37])([CH2:35][CH3:36])[C:30]([O:32][CH2:33]I)=[O:31]>C(Cl)Cl>[NH2:1][CH:2]1[C:15](=[O:16])[N:4]2[C:5]([C:12]([O:14][CH2:33][O:32][C:30](=[O:31])[C:29]([CH3:37])([CH3:28])[CH2:35][CH3:36])=[O:13])=[C:6]([CH2:9][O:10][CH3:11])[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 14459667HCID 14459667, compoundHCID 131717216HCID 131717216, compound

Product 1

HCID 14459722HCID 14459722, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.46 g (6 mmol) of 7-amino-3-methoxymethyl-3-cephem-4-carboxylate were suspended in 30 ml of methylene chloride, and 0.92 ml (6 mmol) of 1,8-diazabicyclo-(5,4,0)-undec-7-ene (DBU) was added at 0° C. After 30 minutes, 1.66 g (6.5 mmol) of iodomethyl 2,2-dimethyl-butyrate (compare preparation example 4) were added, while cooling with ice, and the mixture was subsequently stirred at room temperature for 2 hours. The precipitate which had separated out was filtered off with suction and the crude product was chromatographed (SiO2 ; toluene/ethyl acetate=1:1). 1.2 g (53%) of the title compound were obtained.

Workup

  1. temperaturewhile cooling with ice
  2. customThe precipitate which had separated out
  3. filtrationwas filtered off with suction
  4. customthe crude product was chromatographed (SiO2 ; toluene/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-18fa53b0b44b4592b0758b085f07879c
Source dataset
uspto-grants-1992_03
Patent number
US05100887

Reaction notes

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