Trifluoromethanesulfonic acid, lithium salt → 3-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl ester

HRID 723914ノート

反応式

HRID 723914 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:13])[C:7](=[O:14])[CH2:6][CH2:5]2.[CH3:15][O:16][C:17]([C@@H:19]1[O:21][CH2:20]1)=[O:18].FC(F)(F)S([O-])(=O)=O.[Li+]>C(#N)C>[CH3:15][O:16][C:17](=[O:18])[CH:19]([OH:21])[CH2:20][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[N:8]([CH3:13])[C:7](=[O:14])[CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 3664839Trifluoromethanesulfonic acid, lithium saltHCID 9877347Methyl (2R)-2-oxiranecarboxylateHCID 218777156-amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one

生成物 1

HCID 684917263-(8-Fluoro-1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-ylamino)-2-hydroxypropionic acid methyl ester収率 62%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

6-Amino-8-fluoro-1-methyl-3,4-dihydro-1H-quinolin-2-one (Step 3, 2.25 g, 0.0116 mol), methyl (2R)-glycidate (1.18 g, 0.0116 mol) and lithium trifluoromethanesulfonate (1.81 g, 0.0116 mol) in acetonitrile (10 ml) are heated at 90° C. overnight. The reaction is concentrated and the residue diluted with ethyl acetate, washed with water and saline, dried (MgSO4) and evaporated. The residue is purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a yellow solid (2.13 g, 62%); MS (m/z): [M+H]+=297.

後処理

  1. concentrationThe reaction is concentrated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with water and saline
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-3ef6839eecad474f8a4d155e2ab712ff
出典データセット
uspto-grants-2006_11
特許番号
US07141588B2

反応ノート

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