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

HRID 890925

Reaction equation

HRID 890925 reaction equation
[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

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 74740Phenylmethanesulfonyl chlorideHCID 76551D-Isoleucine

Product 1

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

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9ab69903722b4237ac8c3eb850cc3f90
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Linked notes

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