Triethylamine → methyl-(R)-2-methanesulfonyloxybutyrate

HRID 2197658노트

반응식

HRID 2197658 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 86617529methyl-(R)-2-methanesulfonyloxybutyrate수율 100%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-bac517aa78d14803a1a44bd304f3ded4
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338621B2

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