Hydrochloric Acid → Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

HRID 1648343Notes

Reaction equation

HRID 1648343 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.Cl>C1COCC1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[B:20]([OH:25])[OH:21])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideHCID 178418339Butyllithium

Product 1

HCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11.2 mmol of N-t-butylbenzenesulfonamide (from Step C) in anhydrous THF (20 mL) cooled to -40° C. under N2 was addeel 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to room temperature and stirred for 2 hours. To the mixture, containng the dianion at 0° C., was added triisopropyl borate (3.9 mL, 1.5 equiv). The next day, 2 N HCl (3 mL) was added and the mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic solution was washed with 2N HCl, H2O and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. The material was used in the next step without further purification.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with EtOAc
  5. washThe organic solution was washed with 2N HCl, H2O and brine
  6. dry with materialThe organic phase was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fcbc09359694b569b2d21c577183bbe
Source dataset
uspto-grants-1995_07
Patent number
US05436259

Reaction notes

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