Benzyl Bromide → HCID 14856060, compound

HRID 974272Notes

Reaction equation

HRID 974272 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][NH:4][C:3]=1[C:17]([OH:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([C:17]([O:19][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:18])=[N:4][CH:5]=[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[O:8][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14856051HCID 14856051, compound

Product 1

HCID 14856060HCID 14856060, compoundYield 178.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.96 g of the title compound of Example 1, 5.52 g potassium carbonate and 10.40 g benzylbromide were dissolved in 200 ml DMF and kept at 80°-90° C. for 18 hours. The solvent was then distilled off in vacuo and the oil residue dissolved in 100 ml ethyl acetate and 100 ml water. The organic layer was separated and washed again with 50 ml water. The solvent of the dried organic phase was then stripped off to afford an oily residue (18 g). The oil was dissolved in 30 ml ethyl acetate/cyclohexane (1:1). 4.1 g 3-bromo-1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)- 2-pyridinecarboxylic acid, phenylmethyl ester crystallized from the solution. The filtrate was chromatographed on silica gel using ethylacetate/cyclohexane (1:1) as eluent. Fractions 33-35 contained 4 g pure title compound M.P.=98°-100° C.; another 1.9 g title compound with 10% 3-Bromo-1,4-dihydro-4-oxo-5 -(phenylmethoxy)-1-(phenylmethyl)-2-pyridinecarboxylic acid, phenylmethyl ester were obtained from fractions 57-104.

Workup

  1. distillationThe solvent was then distilled off in vacuo
  2. dissolutionthe oil residue dissolved in 100 ml ethyl acetate
  3. customThe organic layer was separated
  4. washwashed again with 50 ml water

Sources & evidence

ORD record
ord-5595363bf0b0415ca98c077c21c02d69
Source dataset
uspto-grants-1991_11
Patent number
US05068331

Reaction notes

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