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

HRID 639023노트

반응식

HRID 639023 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 61221Dibutyltin oxide촉매HCID 6344Dichloromethane용매HCID 86585896Sodium bicarbonate water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a24824a6d8f6436ba773bee0138d6b6d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

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