Trimethyl borate → Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

HRID 1037688Notes

Reaction equation

HRID 1037688 reaction equation
C([Li])CCC.[C:6]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])([CH3:9])([CH3:8])[CH3:7].[B:20](OC)([O:23]C)[O:21]C.[Cl-].[NH4+]>C1COCC1>[B:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[S:11]([NH:10][C:6]([CH3:9])([CH3:7])[CH3:8])(=[O:13])=[O:12])([OH:23])[OH:21]

Participants

6

Reactant 4

HCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 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

Conditions

Temperature
22 °C

Procedure

27 ml of n-butyllithium (15% solution in n-hexane) are added dropwise at −5° C. to a solution of 4.29 g of N-tert-butylbenzenesulfonamide in 25 ml of THF under argon. The mixture is stirred at 22° C. for 1 h, re-cooled to −5° C., and 2.8 g of trimethyl borate are slowly added dropwise. The mixture is stirred at 22° C. for 3 h, before 100 ml of aqueous ammonium chloride solution is added dropwise. The phases are separated, and the aqueous phase is extracted a further twice with MTB ether. The combined organic phases are dried over magnesium sulfate. Filtered and evaporated to dryness in vacuo.

Workup

  1. temperaturere-cooled to −5° C.
  2. additionis added dropwise
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted a further twice with MTB ether
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationFiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-c34913e7627f4d03aa61b235317838ff
Source dataset
uspto-grants-2013_10
Patent number
US08546565B2

Reaction notes

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