Ethanol → HCID 53694813, compound

HRID 2288010Notes

Reaction equation

HRID 2288010 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:23](O)[CH3:24]>>[CH2:23]([O:17][C:16](=[O:18])[C@@H:12]([CH:13]([CH3:15])[CH3:14])[NH:11][S:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])[CH3:24]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 737247N-[(4-fluorophenyl)sulfonyl]-D-valine

Product 1

HCID 53694813HCID 53694813, compound

Procedure

To a solution of 15.0 g (54 mmol) of N-[(4-fluorophenyl)sulfonyl]-D-valine from Example 1a in 55 mL of anhydrous ethanol cooled in an ice bath, was slowly added 5.0 mL (8.1 g, 68 mmol) of thionyl chloride over 5 minutes. The reaction mixture was then stirred at room temperature for 28 hours, the solvents removed under reduced pressure and the residue dissolved in ethyl acetate. This was then washed with saturated sodium bicarbonate, 5% potassium hydrogen sulfate and brine, dried over sodium sulfate, filtered and concentrated to afford crude product, which was chromatographed on silica gel using 10-20% ethyl acetate/hexane to yield 12.8 g of pure N-[(4-fluorophenyl)sulfonyl]-D-valine ethyl ester, m/e=304 (M+H).

Workup

  1. customover 5 minutes
  2. customthe solvents removed under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThis was then washed with saturated sodium bicarbonate, 5% potassium hydrogen sulfate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford crude product, which
  9. customwas chromatographed on silica gel using 10-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1510ae83afd14fcf90008e48a4e55fb5
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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