Hydrochloric Acid → HCID 19939772, compound

HRID 36109Notes

Reaction equation

HRID 36109 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:5][CH:4]=1)[CH3:2].[Li]CCCC.[B:22]([O:31]C(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl>C1COCC1>[C:13]([S:10]([NH:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][C:7]=1[O:23][B:22]([OH:31])[OH:27])(=[O:12])=[O:11])([CH3:15])([CH3:14])[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 540085744-Ethylphenyl-t-butylsulfonamideHCID 178418339Butyllithium

Product 1

HCID 19939772HCID 19939772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-ethylphenyl-t-butylsulfonamide (6.44 g, 26.7 mmoL) in anhydrous THF (60 mL) cooled to -20° C. under N2 was added 2.5M n-BuLi solution (27 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright orange dianion at 0° C., was added B(OiPr)3 (9.3 mL, 1.5 equiv). The reaction was allowed to warm to rt and stirred overnight. The next day 2N HCl (3 mL) was added and the mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The material was used in subsequent steps without further purification.

Workup

  1. additionTo the mixture, containing the bright orange dianion at 0° C.
  2. temperatureto warm to rt
  3. stirringstirred overnight
  4. stirringthe mixture was stirred for 1 h
  5. customThe solvent was removed under reduced pressure
  6. extractionthe residue was extracted with EtOAc
  7. washThe organic was washed with 2N HCl, H2O and brine
  8. dry with materialThe organic was dried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c3c54aa85d04e1895df6686da50bdac
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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