Water → Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl ester

HRID 1695008노트

반응식

HRID 1695008 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([C@H:12]1[O:16][C:15](=[O:17])[C@H:14]([CH2:18][CH2:19][CH3:20])[CH2:13]1)[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]([O:11][S:29]([CH3:28])(=[O:31])=[O:30])[C@@H:12]1[CH2:13][C@@H:14]([CH2:18][CH2:19][CH3:20])[C:15](=[O:17])[O:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66645875(3R,5S)-5-[(R)-2-Benzyloxy-1-hydroxyethyl]-3-propyldihydrofuran-2-one

생성물 1

HCID 86636126Methanesulfonic acid (R)-2-benzyloxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl ester수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 12.1 g of (3R,5S)-5-[(R)-2-benzyloxy-1-hydroxyethyl]-3-propyldihydrofuran-2-one obtained in Example (116c) (43.5 mmol) in methylene chloride (300 ml) was cooled in an ice bath. Then, 13.2 g of triethylamine (131 mmol) and 7.30 g of methanesulfonyl chloride (63.7 mmol) were added thereto, and the mixture was stirred at the same temperature for one hour. 500 ml of water was added to the reaction mixture, followed by extraction with methylene chloride. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=4/1-1/1) to obtain 15.2 g of the title compound (yield: quant.).

후처리

  1. extractionfollowed by extraction with methylene chloride
  2. washThen, the organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=4/1-1/1)

출처 및 근거

ORD 기록
ord-768d2577fe3b4f658c8dbc8d86e44306
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158790B2

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