Triethylamine → methyl-(R)-2-methanesulfonyloxybutyrate

HRID 2197658ノート

反応式

HRID 2197658 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8](=[O:13])[C@H:9]([OH:12])[CH2:10][CH3:11].C(N(CC)CC)C.CC1CCCCC1.C(OCC)(=O)C>ClCCl.O>[CH3:6][O:7][C:8](=[O:13])[C@H:9]([O:12][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH3:11]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11701033(R)-Methyl 2-hydroxybutanoateHCID 66985183Ethyl acetate methylcyclohexane

生成物 1

HCID 86617529methyl-(R)-2-methanesulfonyloxybutyrate収率 100%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of methanesulfonic acid chloride (5.33 g, 46.5 mmol, 1.1 equiv.) in dichloromethane (50 ml, 11 vol.) cooled to 0-5° C. is added over a period of 30 min. a mixture of methyl-(R)-2-hydroxybutyrate (5.1 g, 43.2 mmol, 1 equiv.) and triethylamine (4.7 g, 46.5 mmol, 1.1 equiv.) in dichloromethane (25 ml). When conversion is complete (TLC: methylcyclohexane/ethyl acetate=1/1 (v/v), dying with molybdatophosphoric acid; Rf=0.5), the mixture is allowed to warm to room temperature and 50 ml of water is added. The two resulting layers are separated and the organic layer is washed with 50 ml of water. The organic layer is dried over sodium carbonate and concentrated under reduced pressure to afford methyl-(R)-2-methanesulfonyloxybutyrate (IIg) as yellow oil (8.5 g, 43.2 mmol, 100%)

後処理

  1. additionis added over a period of 30 min.
  2. customThe two resulting layers are separated
  3. washthe organic layer is washed with 50 ml of water
  4. dry with materialThe organic layer is dried over sodium carbonate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bac517aa78d14803a1a44bd304f3ded4
出典データセット
uspto-grants-2012_12
特許番号
US08338621B2

反応ノート

読み込み中…