4-Toluenesulfonyl chloride → 2-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

HRID 639023

反応式

HRID 639023 の反応式
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([OH:15])[CH2:13][OH:14])=[N:9][C:8]([O:16][CH3:17])=[CH:7][CH:6]=2.C(N(CC)CC)C.[S:25](Cl)([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26]>ClCCl.O.C(=O)(O)[O-].[Na+].C([Sn](=O)CCCC)CCC>[CH3:32][C:31]1[CH:33]=[CH:34][C:28]([S:25]([O:14][CH2:13][CH:12]([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:16][CH3:17])[N:9]=3)[N:4]=[CH:3][C:2]=2[F:1])[OH:15])(=[O:27])=[O:26])=[CH:29][CH:30]=1

参加物

7

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 671345911-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol

生成物 1

HCID 866033622-[3-Fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-2-hydroxyethyl 4-methylbenzenesulfonate収率 75%

試薬・触媒・溶媒 3

HCID 61221Dibutyltin oxide触媒HCID 6344Dichloromethane溶媒HCID 86585896Sodium bicarbonate water溶媒

実験手順

To a solution of 1-[3-fluoro-6-(methoxy)-1,5-naphthyridin-4-yl]-1,2-ethanediol (16.5 g, 71 mmol)) in dichloromethane (200 mL), triethylamine (10 mL) and dibutyltin oxide (350 mg) was added tosyl chloride (13.2 g). After 3 hours, the mixture was diluted with water/sodium bicarbonate and extracted several times with chloroform. The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 20-30% ethyl acetate in chloroform to afford the desired product (20.3 g, 75%). MS (+ve ion electrospray) m/z 393 (M+H)+.

後処理

  1. extractionextracted several times with chloroform
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated under vacuum
  4. customThe residue was chromatographed on silica gel eluting with 20-30% ethyl acetate in chloroform

出典と根拠

ORDレコード
ord-a24824a6d8f6436ba773bee0138d6b6d
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

関連ノート

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