4-(Hydroxymethyl)-2-Isopropylthiazole → N-((2-Isopropyl-4-thiazolyl)methoxycarbonyl)valine Methyl Ester

HRID 433752

反応式

HRID 433752 の反応式
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[S:6][CH:7]=1.[CH3:11][O:12][C:13](=[O:22])[C@:14]([N:19]=[C:20]=[O:21])([CH:16]([CH3:18])[CH3:17])N>CN(C)C1C=CN=CC=1.ClCCl>[CH3:11][O:12][C:13](=[O:22])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:19][C:20]([O:1][CH2:2][C:3]1[N:4]=[C:5]([CH:8]([CH3:10])[CH3:9])[S:6][CH:7]=1)=[O:21]

参加物

5

反応物 2

HCID 105349374-(Hydroxymethyl)-2-IsopropylthiazoleHCID 22845662a-Isocyanato-valine methyl ester

生成物 1

HCID 10781571N-((2-Isopropyl-4-thiazolyl)methoxycarbonyl)valine Methyl Ester収率 57%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 2.18 g (15 mmol) of 4-(hydroxymethyl)-2-isopropylthiazole, 15.8 mmol of α-isocyanato-valine methyl ester and 1.5 mmol of 4-dimethylaminopyridine in 75 ml of dichloromethane was heated at reflux for 5 h. The resulting solution was washed successively with 10% citric acid, aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo. Silica gel chromatography of the residue using 5% ethyl acetate in chloroform provided 2.67 g (57%) of the pure desired compound, Rf 0.46 (4% methanol in chloroform). NMR 1H NMR (DMSO-d6) δ 1.26 (d, J=8 Hz, 3H), 1.32 (d, J=7 Hz, 6H), 3.27 (heptet, J=7 Hz, 1H), 3.63 (s, 3H), 4.10 (pentet, J=8 Hz, 1H), 5.02 (s, 2H), 7.47 (s, 1H), 7.81 (d, J=8 Hz, 1H). Mass spectrum: (M+H)+=287.

後処理

  1. temperatureat reflux for 5 h
  2. washThe resulting solution was washed successively with 10% citric acid, aqueous NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6a6aa7c8902746cd96c91c42fedbb216
出典データセット
uspto-grants-2003_12
特許番号
US06667404B2

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