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

HRID 265848Notes

Reaction equation

HRID 265848 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 purification 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
  4. customin vacuo and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-9f1622f7f3e84a6e99212258a19a1082
Source dataset
uspto-grants-1997_07
Patent number
US05648497

Reaction notes

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