Lithium aluminum hydride → Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide

HRID 1397846ノート

反応式

HRID 1397846 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12])[C:5]=1[F:17].[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:17][C:5]1[C:4]([CH2:3][OH:2])=[CH:9][CH:8]=[CH:7][C:6]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12]

参加物

5

反応物 3

HCID 28112Lithium aluminum hydrideHCID 62649Sodium sulfate decahydrateHCID 579632422-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

生成物 1

HCID 58087499Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide収率 87.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester (20, 3.80 g, 13.8 mmol) in 133 mL of tetrahydrofuran, lithium tetrahydroaluminate (1.00 M in tetrahydrofuran, 20.0 mL, 20.0 mmol) was added under an atmosphere of nitrogen at room temperature. The reaction was stirred at room temperature for 8 hours, followed by addition of 10 g of sodium sulfate decahydrate. After 12 hours, the reaction was filtered, the filtrate concentrated under vacuum and purified with silica gel column chromatography eluting with 5% methanol in dichloromethane to give the desired compound as a white solid (21, 3.0 g, 87.9%).

後処理

  1. waitAfter 12 hours
  2. filtrationthe reaction was filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. custompurified with silica gel column chromatography
  5. washeluting with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-e41ede936f744a73a10d687a43b3ded3
出典データセット
uspto-grants-2014_12
特許番号
US08901301B2

反応ノート

読み込み中…