Hydrochloric Acid → N-(benzylsulfonyl)-D-isoleucine

HRID 890925

반응식

HRID 890925 반응식
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C@@H:3]([CH2:5][CH3:6])[CH3:4].[CH2:10]([S:17](Cl)(=[O:19])=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>O1CCOCC1.[OH-].[Na+]>[CH2:10]([S:17]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[C@@H:3]([CH2:5][CH3:6])[CH3:4])(=[O:19])=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 74740Phenylmethanesulfonyl chlorideHCID 76551D-Isoleucine

생성물 1

HCID 36688801N-(benzylsulfonyl)-D-isoleucine수율 97%

시약·촉매·용매 2

HCID 14798Sodium Hydroxide용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of D-isoleucine (3 g, 22.9 mmol) in dioxane (184 ml), 1N aqueous sodium hydroxide (23 ml) and then benzylsulfonyl chloride (6 g, 34.4 mmol) were added and stirred at room temperature. After 3 hours, the reaction mixture was adjusted to pH 2 with 2N aqueous hydrogen chloride and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated under reduced pressure and the residue was applied to flash column chromatography (Merck Silicagel 60; mobile phase: dichloromethane:methanol=10:1, 4:1) to give N-(benzyl-sulfonyl)-D-isoleucine (6.3 g, 22.2 mmol; yield 97%).

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter magnesium sulfate was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9ab69903722b4237ac8c3eb850cc3f90
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001887B2

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