Hydrogen Bromide → HCID 67396240, compound

HRID 70669Notes

Reaction equation

HRID 70669 reaction equation
Br.[C:2]([C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:31]2[N:36]=[C:35]([O:37]C)[C:34]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:33][CH:32]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].O>O1CCOCC1>[C:2]([C:6]1[CH:7]=[CH:8][C:9](/[C:12](/[C:31]2[NH:36][C:35](=[O:37])[C:34]([CH2:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:33][CH:32]=2)=[CH:13]\[C@H:14]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 674013833-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)propanoic acid

Product 1

HCID 67396240HCID 67396240, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (1.7 mL) was added to a solution of 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)propanoic acid (172 mg) in 1,4-dioxane (1.7 mL), and the mixture was stirred at 65° C. for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give 3-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-oxo-1,2-dihydropyridin-3-yl)propanoic acid as a yellow oil (153 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record
ord-c7ca81712562405aa8377383382bd284
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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