Water → HCID 86658012, compound

HRID 70664Notes

Reaction equation

HRID 70664 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[C:13]([C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[C:42]2[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][CH2:50][CH2:51][OH:52])=[C:44]([O:53][CH3:54])[N:43]=2)=[CH:24]\[C@@H:25]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=3[O:39][CH3:40])[C:28](=[O:41])[CH2:27][CH2:26]2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].O>C(Cl)(Cl)Cl>[CH3:8][S:9]([O:52][CH2:51][CH2:50][CH2:49][CH2:48][C:45]1[C:44]([O:53][CH3:54])=[N:43][C:42](/[C:23](/[C:20]2[CH:21]=[CH:22][C:17]([C:13]([CH3:16])([CH3:14])[CH3:15])=[CH:18][CH:19]=2)=[CH:24]/[C@H:25]2[CH2:26][CH2:27][C:28](=[O:41])[N:29]2[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[O:39][CH3:40])=[CH:47][CH:46]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 67397159(5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

Product 1

HCID 86658012HCID 86658012, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (50 μL) and methanesulfonyl chloride (25 μL) were added to a solution of (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(4-hydroxybutyl)-6-methoxypyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (144 mg) in chloroform (2 mL), and the mixture was stirred at room temperature for three hours. Triethylamine (50 μL) and methanesulfonyl chloride (25 μL) were further added thereto and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 4-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)butyl methanesulfonate as a crude product. 2 M dimethylamine (solution in methanol) (3 mL) was added to 4-(6-{(E)-1-(4-tert-butylphenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-2-methoxypyridin-3-yl)butyl methanesulfonate, and the mixture was stirred at room temperature for 17 hours. The solvent was evaporated from the reaction solution and then water was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0→4:1) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-{5-[4-(dimethylamino)butyl]-6-methoxypyridin-2-yl}ethenyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4f7101e47a2b434f9ab3c690b4ec7db4
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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