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

HRID 274823Notes

Reaction equation

HRID 274823 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-dimethylbutyrate (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-bca7eaf8bbfb4c2cbfd37111ded30cce
Source dataset
uspto-grants-1995_02
Patent number
USRE034865

Reaction notes

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