Hydrochloric Acid → 4-(Morpholin-4-ylsulphonyl)benzeneboronic acid

HRID 1726878Notes

Reaction equation

HRID 1726878 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.[Li]CCCC.Cl>C1COCC1.CCCCCC>[N:11]1([S:8]([C:5]2[CH:6]=[CH:7][C:2]([B:17]([OH:22])[OH:18])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 38002234-(4-Iodophenyl)sulfonylmorpholineHCID 178418339Butyllithium

Product 1

HCID 441195464-(Morpholin-4-ylsulphonyl)benzeneboronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a solution of 25 g of the compound obtained in Step A (70.8 mmol) and 26 ml of triisopropyl borate in 400 ml of THF cooled to −60° C. there are added, dropwise, over 45 minutes and under a gentle current of nitrogen, 53 ml of a 1.6M solution of BuLi (84.9 mmol) in hexane. The reaction solution is then stirred for 1 hour 30 minutes at −60° C. and is subsequently returned to ambient temperature over 2 hours. The reaction mixture is treated with about 100 ml of 1N HCl and is extracted 3 times with ethyl acetate. The organic phases are collected, washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue obtained is chromatographed on an SiO2 column, eluting with CH2Cl2 and then with a mixture of CH2Cl2/MeOH 98/2 and then 95/5. After evaporation of the fractions, the residue is triturated in ethyl ether to yield the title product after filtration.

Workup

  1. additionare added
  2. waitis subsequently returned to ambient temperature over 2 hours
  3. extractionis extracted 3 times with ethyl acetate
  4. customThe organic phases are collected
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe residue obtained
  9. customis chromatographed on an SiO2 column
  10. washeluting with CH2Cl2
  11. additionwith a mixture of CH2Cl2/MeOH 98/2
  12. customAfter evaporation of the fractions
  13. customthe residue is triturated in ethyl ether

Sources & evidence

ORD record
ord-e0f2c65fff144a3a921563260a6639e6
Source dataset
uspto-grants-2009_02
Patent number
US07494994B2

Reaction notes

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