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

HRID 890925

反応式

HRID 890925 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 74740Phenylmethanesulfonyl chlorideHCID 76551D-Isoleucine

生成物 1

HCID 36688801N-(benzylsulfonyl)-D-isoleucine収率 97%

試薬・触媒・溶媒 2

HCID 14798Sodium Hydroxide溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9ab69903722b4237ac8c3eb850cc3f90
出典データセット
uspto-grants-2006_02
特許番号
US07001887B2

関連ノート

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