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

HRID 235513Notes

Reaction equation

HRID 235513 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-59c52b0ed5b7448fb6c63c482d60fe4f
Source dataset
uspto-grants-1997_01
Patent number
US05597926

Reaction notes

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