N-bromobutanimide → t-Butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate 1-oxide

HRID 2052098Notes

Reaction equation

HRID 2052098 reaction equation
[Br:1][CH:2]1[C:7]([CH3:8])=[C:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[N:5]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:4]2[S:3]1=[O:29].[Br:30]N1C(=O)CCC1=O>C(Cl)Cl.[W]>[Br:1][CH:2]1[C:7]([CH2:8][Br:30])=[C:6]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[N:5]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C@H:4]2[S:3]1=[O:29]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 70463804t-Butyl 2-bromo-3-methyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 70463952t-Butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate 1-oxideYield 26.2%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 6344DichloromethaneSolvent

Procedure

The reference 2-bromo-3-bromomethyl compound in the above HPLC analysis was prepared as follows: To a solution of 4.6 g (9.5 mmoles) of t-butyl 2-bromo-7-phenylacetamido-3-methyl-3-cephem-4-carboxylate 1-oxide in 350 ml of methylene chloride cooled in ice and irradiated with a 150 W tungsten lamp were added in portions over a period of 105 minutes 3.05 g (17.1 mmoles) of N-bromosuccinimide. After the addition was completed, the irradiation was continued for another hour and the orange-colored solution was concentrated to dryness by evaporation at low temperature. The residue was chromatographed on silica gel (elution with methylene chloride/acetone; first 72:1, then 49:1, v/v) to obtain 1.4 g (26%) of t-butyl 2-bromo-3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate 1-oxide.

Workup

  1. additionAfter the addition
  2. customthe irradiation
  3. waitwas continued for another hour
  4. concentrationthe orange-colored solution was concentrated to dryness by evaporation at low temperature
  5. customThe residue was chromatographed on silica gel (
  6. washelution with methylene chloride/acetone

Sources & evidence

ORD record
ord-b6b248f5e9ca4eaa897c63280f90e4fc
Source dataset
uspto-grants-1980_01
Patent number
US04182870

Reaction notes

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