Sulfuric Acid → HCID 23657565, compound

HRID 2287996Notes

Reaction equation

HRID 2287996 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.[CH3:19][C:20](=[CH2:22])[CH3:21].OS(O)(=O)=O>C(Cl)Cl.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@@H:12]([C:16]([O:18][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 737247N-[(4-fluorophenyl)sulfonyl]-D-valine

Product 1

HCID 23657565HCID 23657565, compound

Reagents, catalysts & solvents 1

HCID 18626912Dioxane methylene chlorideSolvent

Procedure

A solution of N-[(4-fluorophenyl)-sulfonyl]-D-valine from Example 1a (8.00 g, 29.1 mmol) in CH2Cl2 /dioxane was treated with isobutylene in the presence of H2SO4 at room temperature at a pressure of 18 psi. The reaction was quenched by adding the solution to a mixture of NaHCO3 (20 g) in water (300 mL) cooled in an ice bath. The mixture was extracted with ethyl acetate. The ethyl acetate layers were combined and washed with H2O and brine, dried over MgSO4, and concentrated to a solid. Recrystallization from diethyl ether/hexane afforded N-[(4-fluorophenyl)-sulfonyl]-D-valine, 1,1-dimethylethyl ester, as a white solid (6.99 g, 73%): MS MH+ calc'd for Cl5H22NO4SF: 332, found: 332. Anal. calc'd for Cl5H22NO4SF: C, 54.36; H, 6.69; N, 4.23. Found: C, 54.21; H, 6.86; N, 4.14.

Workup

  1. customThe reaction was quenched
  2. additionby adding the solution
  3. additionto a mixture of NaHCO3 (20 g) in water (300 mL)
  4. temperaturecooled in an ice bath
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed with H2O and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to a solid
  9. customRecrystallization from diethyl ether/hexane

Sources & evidence

ORD record
ord-8b3e6f209cca48abb0bbe11e32086417
Source dataset
uspto-grants-2000_07
Patent number
US06087359

Reaction notes

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