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

HRID 2230779Notes

Reaction equation

HRID 2230779 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7]([NH:11][SH:12](=[O:14])=[O:13])([CH3:10])([CH3:9])[CH3:8].C([Li])CCC.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.Cl>C1COCC1.CCCCCC>[C:7]([NH:11][S:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[B:24]([OH:25])[OH:23])(=[O:14])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 178418339ButyllithiumHCID 178449957HCID 178449957, compound

Product 1

HCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-Yield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 206.5 g (0.968 mol) of benzene-(N-t-butyl)sulfonamide in 2500 mL of THF under N2 was added 790 mL (1.98 mol) of 2.5M n-butyllithium in hexane over 35 minutes, keeping the temperature between 0-5° C. The reaction mixture was allowed to warm to 10° C., at which time a thick precipitate formed. Triisopropylborate (305 mL, 1.32 mol) was added keeping the temperature below 35° C. After 1 hour, the reaction mixture was cooled, 1N HCl (1570 mL) was added, and the mixture was stirred overnight. The mixture was extracted with 400 mL of ether three times, and the combined organic extracts were extracted with 500 mL of 1N NaOH three times. The aqueous extracts were acidified to pH 1 with 6N HCl and then extracted with 500 mL ether three times. The combined ether extracts were dried over MgSO4, and the solvents evaporated in vacuo until the volume was 700 mL. Hexane (150 mL) was added and overnight, a white precipitate formed. The solid was collected and washed with 10% ether/hexane (250 mL), then dried in vacuo to give 216.3 g (87%) of the desired compound as white crystals. m.p. 118-119° C.; 1H NMR (CDCl3): δ8.00 (d, 1H); 7.82 (d, 1H); 7.53 (m, 2H); 6.29 (br s, 2H); 5.13 (s, 1H); 1.18 (s, 9H).

Workup

  1. custombetween 0-5° C
  2. customformed
  3. customthe temperature below 35° C
  4. temperaturethe reaction mixture was cooled
  5. extractionThe mixture was extracted with 400 mL of ether three times
  6. extractionthe combined organic extracts were extracted with 500 mL of 1N NaOH three times
  7. extractionextracted with 500 mL ether three times
  8. dry with materialThe combined ether extracts were dried over MgSO4
  9. customthe solvents evaporated in vacuo until the volume
  10. additionHexane (150 mL) was added and overnight
  11. customa white precipitate formed
  12. customThe solid was collected
  13. washwashed with 10% ether/hexane (250 mL)
  14. customdried in vacuo

Sources & evidence

ORD record
ord-6176dbe8ea4c49df9b73572d2a842d43
Source dataset
uspto-grants-2002_07
Patent number
US06426346B1

Reaction notes

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