Methyl 2-bromopropionate → methyl(E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoate

HRID 424355Notes

Reaction equation

C([O-])(=O)C.[Na+].[CH3:6][O:7][C:8](=[O:12])[CH:9](Br)[CH3:10].[CH3:13][O:14][C:15]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[C:16]=1/[CH:17]=[CH:18]/[S:19]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:30][CH3:31])=[C:27]([NH2:29])[CH:28]=1)(=[O:21])=[O:20]>CO>[CH3:13][O:14][C:15]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[C:16]=1/[CH:17]=[CH:18]/[S:19]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:30][CH3:31])=[C:27]([NH:29][CH:9]([CH3:10])[C:8]([O:7][CH3:6])=[O:12])[CH:28]=1)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Sodium acetate (0.4 mol) was dissolved in methanol (200 mL). Methyl-2-bromopropionate (40 mmol) was added and the resulting mixture was heated at reflux for 10 min. The heated mixture was cooled to room temperature (25° C.), and (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxybenzenamine (0.1 mol) was added. The resulting mixture was heated at reflux for 1 h. The hot reaction mixture was allowed to cool to room temperature (25° C.), and then poured into ice water (500 mL). A solid precipitate formed. The precipitate was separated by filtration and recrystallized from ethanol to provide the desired methyl(E)-2-(5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenylamino)propanoate.

Workup

temperaturethe resulting mixture was heated
temperatureat reflux for 10 min
additionwas added
temperatureThe resulting mixture was heated
temperatureat reflux for 1 h
customA solid precipitate formed
customThe precipitate was separated by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-41c1bd4802a94b8a8b46f77e775630f2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106033B2

Reaction notes

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