6-Methyl-2-pyridylmethanol → (6-methylpyridin-2-yl)methoxycarbonyl-Valine methyl ester

HRID 742924Notes

Reaction equation

HRID 742924 reaction equation
[N-:1]=[C:2]=[O:3].[CH3:4][O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])N.[CH3:13][C:14]1[N:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[CH3:4][O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])[NH:1][C:2]([O:21][CH2:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:13])[N:19]=1)=[O:3]

Participants

5

Reactant 3

HCID 707366-Methyl-2-pyridylmethanolHCID 94285Valine methyl esterHCID 105034Isocyanate

Product 1

HCID 70051254(6-methylpyridin-2-yl)methoxycarbonyl-Valine methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the isocyanate derived from Valine methyl ester (17.9 mmol) dissolved in toluene was added 6-methyl-pyridine-2-methanol (2.42 g, 1.1 equivalent). The solution was heated at reflux for 2 hours. After concentration in vacuo and purifiction by silica gel column chromatography, (6-methylpyridin-2-yl )methoxycarbonyl-Valine methyl ester (2.8 g) was obtained. Hydrolysis of the methyl ester using aqueous lithium hydroxide provide the title compound upon recrystallization from hot ethyl acetate.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 hours
  3. concentrationAfter concentration in vacuo and purifiction by silica gel column chromatography

Sources & evidence

ORD record
ord-f2b38fb66ee9479fb940e08235fde472
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

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