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

HRID 53916

반응식

HRID 53916 반응식
[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]

참가 물질

4

반응물 2

HCID 11474PiconolHCID 22845662a-Isocyanato-valine methyl ester

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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. 1H NMR (CDCl3) δ 0.91 (d, J=7 Hz, 3 H), 0.98 (d, J=7 Hz, 3 H), 2.19 (m, 1 H), 3.75 (s, 3 H), 4.32 (dd, J=9, 5 Hz, 1 H), 5.24 (s, 2 H), 5.39 (br d, 1 H), 7.23 (ddd, J=8, 4, 1 Hz, 1 H), 7.37 (d, J=8 Hz, 1 H), 7.70 (td, J=8, 2 Hz, 1 H), 8.60 (br d, 1 H). Mass spectrum: (M+H)+ =267.

후처리

  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

출처 및 근거

ORD 기록
ord-279d81b72ffb4333b9ee2e593dddef6a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621109

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