Hydrogen Bromide → HCID 58452340, compound

HRID 70652Notes

Reaction equation

HRID 70652 reaction equation
Br.[C:2]([C:5]1[CH:6]=[CH:7][C:8](/[C:13](/[C:32]2[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[CH:14]/[C@@H:15]2[N:19](CC3C=CC(OC)=CC=3OC)[C:18](=[O:31])[CH2:17][CH2:16]2)=[N:9][C:10]=1[O:11]C)(=[O:4])[CH3:3].O>O1CCOCC1>[C:2]([C:5]1[C:10](=[O:11])[NH:9][C:8](/[C:13](/[C:32]2[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=2)=[CH:14]/[C@H:15]2[CH2:16][CH2:17][C:18](=[O:31])[NH:19]2)=[CH:7][CH:6]=1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 67400682(5R)-5-[(E)-2-(5-acetyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Product 1

HCID 58452340HCID 58452340, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

48% hydrobromic acid (3.0 mL) was added to a solution of (5R)-5-[(E)-2-(5-acetyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (300 mg) in 1,4-dioxane (3.0 mL), and the mixture was stirred at 65° C. for 0.5 hour. 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. Anisole (2 mL) was added to a solution of the residue (278 mg) in trifluoroacetic acid (1 mL), and the mixture was stirred at 80° C. for 4.5 hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give the title compound as a yellow powder (103 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. additionAnisole (2 mL) was added to a solution of the residue (278 mg) in trifluoroacetic acid (1 mL)
  6. stirringthe mixture was stirred at 80° C. for 4.5 hours
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)

Sources & evidence

ORD record
ord-fbe3ac8493214ed6831229697db28e00
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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