反応式
[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[OH:20])[CH2:10][CH2:9][S:8][CH2:7][CH2:6]1)=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([NH:11][C:12](=[O:21])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[O:20][CH:29]([CH3:31])[CH3:30])[CH2:6][CH2:7][S:8][CH2:9][CH2:10]1)=[O:4]参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a suspension of 4-(2-hydroxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester (27) (98 mg, 0.32 mmol), anhydrous Cs2CO3 (208 mg, 0.64 mmol), and KI (11 mg, 0.06 mmol) in DMF (5 mL) is added 2-bromopropane (150 μL, 1.6 mmol). The resulting reaction suspension is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (20 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (80 g silica gel, gradient elution: 5-40% EtOAc in heptane) to give a pure product (28) as white solid (92 mg, 81%).
後処理
- customThe resulting reaction suspension
- customAfter the removal of DMF in vacuo
- dissolutionthe residue is dissolved in EtOAc (20 mL)
- washwashed with water (1×5 mL) and brine (2×5 mL)
- dry with materialThe organic layer is dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue is purified by flash column chromatography (80 g silica gel, gradient elution: 5-40% EtOAc in heptane)
出典と根拠
- ORDレコード
- ord-dc112b9fcc0246cba4432651c7307afc
- 出典データセット
- uspto-grants-2013_10
- 特許番号
- US08569535B2
関連ノート
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