Diallylamine → 2-(Diallylamino)-2-(4-(methoxymethyl)phenyl)acetic acid

HRID 2202332Notes

Reaction equation

HRID 2202332 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.O.[C:14]([OH:18])(=[O:17])[CH:15]=O.[CH2:19]([NH:22][CH2:23][CH:24]=[CH2:25])[CH:20]=[CH2:21]>C(#N)C>[CH2:19]([N:22]([CH2:23][CH:24]=[CH2:25])[CH:15]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][O:2][CH3:1])=[CH:5][CH:6]=1)[C:14]([OH:18])=[O:17])[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 31279DiallylamineHCID 37238124-(Methoxymethyl)benzeneboronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 1186227072-(Diallylamino)-2-(4-(methoxymethyl)phenyl)acetic acidYield 12.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (4-(methoxymethyl)phenyl)boronic acid (999 mg, 6.02 mmol), glyoxylic acid monohydrate (554 mg, 6.02 mmol) and diallylamine (0.741 mL, 6.02 mmol) in acetonitrile (12 mL) was stirred at 60° C. for 5 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Diol, solvent; ethyl acetate), and crystallized from ethyl acetate/hexane to give 2-(diallylamino)-2-(4-(methoxymethyl)phenyl)acetic acid (200 mg, 0.726 mmol, 12.07%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (Diol, solvent; ethyl acetate)
  3. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-911d99c4b7634b01a47f05a190c831ac
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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