Water → HCID 737246, compound

HRID 1794559Notes

Reaction equation

HRID 1794559 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].O.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.CCCCCC>[OH-].[Na+].O1CCCC1.CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 962WaterHCID 6287L-ValineHCID 8058HexaneHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 737246HCID 737246, compoundYield 62.6%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Valine (11.7 g, 100 mmol) was dissolved in 1M aqueous sodium hydroxide (100 mL), and then purified water (150 mL) and tetrahydrofuran (100 mL) were added thereto. The solution was stirred under ice-cooling, and to the solution were dropwise added 1M aqueous sodium hydroxide (100 mL) and a solution of 4-fluorobenzenesulfonyl chloride (17.5 g, 90 mmol) in tetrahydrofuran (100 mL) simultaneously. The mixed solution was stirred and allowed to react at room temperature for 18 hours. After completion of the reaction, the pH was adjusted to 2 to 3, and the solution was extracted with ethyl acetate. The extract was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to remove ethyl acetate. The residue was washed with a hexane-ethyl acetate mixture (prepared by mixing about 10 to 20 fold amount of hexane with 1 fold amount of ethyl acetate; hereinafter referred to as hexane-ethyl acetate mixture) to give N-((4-fluorophenyl)sulfonyl)-L-valine (15.5 g, 56% yield) as white crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixed solution was stirred
  3. customto react at room temperature for 18 hours
  4. customAfter completion of the reaction
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe extract was washed successively with dilute hydrochloric acid and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto remove ethyl acetate
  10. washThe residue was washed with a hexane-ethyl acetate mixture (
  11. customprepared

Sources & evidence

ORD record
ord-fe826aeee558448591dbb1d1b277054b
Source dataset
uspto-grants-2006_04
Patent number
US07022738B2

Reaction notes

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