2-Ketobutyric acid methyl ester → Methyl 2-[3-(1,3-dioxolan-2-yl)-2-fluoro-4-pyridinyl]-2-hydroxybutanoate

HRID 1635072

反応式

HRID 1635072 の反応式
C([Li])CCC.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[C:12]([F:18])=[N:13][CH:14]=[CH:15][C:16]=1I.[O:19]=[C:20]([CH2:25][CH3:26])[C:21]([O:23][CH3:24])=[O:22].O.C1COCC1>CCCCCC.C1COCC1>[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[C:12]([F:18])=[N:13][CH:14]=[CH:15][C:16]=1[C:20]([OH:19])([CH2:25][CH3:26])[C:21]([O:23][CH3:24])=[O:22]

参加物

7

反応物 4

HCID 5451272-Ketobutyric acid methyl esterHCID 21881883Oxolane--water (1/1)HCID 227449983-(1,3-Dioxolan-2-yl)-2-fluoro-4-iodopyridineHCID 178418339Butyllithium

生成物 1

HCID 22745040Methyl 2-[3-(1,3-dioxolan-2-yl)-2-fluoro-4-pyridinyl]-2-hydroxybutanoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

6.9 ml (11 mmol) of 1.6M butyllithium in hexane are added dropwise to a solution, stirred at −78° C. under an argon atmosphere, of 3.1 g (11 mmol) of 3-(1,3-dioxolan-2-yl)-2-fluoro-4-iodopyridine in 100 ml of THF. The reaction mixture is then stirred for 10 minutes at −78° C. before the dropwise addition of a solution of 1.5 g (13 mmol) of methyl 2-oxo-butyrate in 20 ml of THF. The mixture is stirred for 3 hours at −78° C., hydrolysed with a mixture of water/THF, and decanted. The aqueous phase is extracted 3 times with 50 ml of ethyl acetate each time, and the combined organic phases are dried over magnesium sulphate and then concentrated. The expected product is obtained by purification of the residue by chromatography over silica (eluant:dichloromethane/acetone 95/5).

後処理

  1. customdecanted
  2. extractionThe aqueous phase is extracted 3 times with 50 ml of ethyl acetate each time
  3. dry with materialthe combined organic phases are dried over magnesium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-21201123a2ed45faac3cdf7cea47f375
出典データセット
uspto-grants-2003_01
特許番号
US06509345B2

関連ノート

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