Dichloromethane → t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

HRID 1668538ノート

反応式

HRID 1668538 の反応式
ClCCl.[OH:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O>[CH3:32][S:33]([O:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=1)(=[O:35])=[O:34]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58105232t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate

生成物 1

HCID 58105230t-Butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 200 mL round-bottom flask, 50 mL of dichloromethane, 2.78 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pentanoate and 2.0 g of diisopropylethylamine were added, and the mixture was stirred at ice temperature for 10 minutes. To the reaction mixture, 0.89 mL of methanesulfonyl chloride was added dropwise, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was partitioned. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1) to give 2.28 g of t-butyl 5-(6-methane-sulfonyloxymethylpyridin-2-yl)pentanoate as a yellow oil.

後処理

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customthe mixture was partitioned
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-2baea6e96b8544059ce63e17b1a5ff9a
出典データセット
uspto-grants-2011_08
特許番号
US07989446B2

反応ノート

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