Triethylamine → Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl ester

HRID 456597노트

반응식

HRID 456597 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15](=[O:17])[NH:14][C:13]=2[CH:18]=1.C(N(CC)CC)C>O1CCCC1>[O:17]=[C:15]1[NH:14][C:13]2[CH:18]=[C:9]([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:10]=[CH:11][C:12]=2[O:16]1

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chloride2회HCID 179812295-(2-Hydroxy-ethyl)-3H-benzoxazol-2-one

생성물 1

HCID 86760443Methanesulfonic acid 2-(2-oxo-2,3-dihydro-benzooxazol-5-yl)-ethyl ester수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methanesulfonyl chloride (0.23 ml, 2.93 mmol) was added dropwise, at room temperature, to a solution of alcohol (b) (0.5 g, 2.79 mmol) and triethylamine (0.41 ml, 3 mmol) in tetrahydrofuran (20 ml) and the mixture was stirred for 3 hours. More methane sulfonyl chloride (0.1 ml) and triethylamine (0.1 ml) were added and stirring was continued over night. The same amount of reagent was added yet again and stirring continued for 2 hours. The solvent was then concentrated, the residue was suspended in water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated. The solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1) to give the product (0.2 g, 28%).

후처리

  1. stirringstirring
  2. waitwas continued over night
  3. additionThe same amount of reagent was added yet again
  4. stirringstirring
  5. waitcontinued for 2 hours
  6. concentrationThe solvent was then concentrated
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe solid residue was chromatographed on silica gel eluting with heptane-ethyl acetate (1-1)

출처 및 근거

ORD 기록
ord-771d18febf8d47fd9363ab5311ab34fe
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186730B2

반응 노트

불러오는 중…