Piconol → N-((2-Pyridinyl)methoxycarbonyl)valine Methyl Ester

HRID 2210941Notes

Reaction equation

HRID 2210941 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@:4]([N:9]=[C:10]=[O:11])([CH:6]([CH3:8])[CH3:7])N.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][OH:20]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:9][C:10]([O:20][CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 11474PiconolHCID 22845662a-Isocyanato-valine methyl ester

Product 1

HCID 10378230N-((2-Pyridinyl)methoxycarbonyl)valine Methyl EsterYield 54.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.78 g (5.0 mmol) of α-isocyanato-valine methyl ester and 0.55 ml (5.7 mmol) of pyridine-2-methanol in 30 mL of toluene was heated at reflux under N2 atmosphere for 4 h. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography using 2% methanol in chloroform to give 0.72 g (54%) of the desired compound as an oil.

Workup

  1. temperatureat reflux under N2 atmosphere for 4 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0cd2362ced4e4be9a5fa6987ea0cfa9e
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Reaction notes

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