N-(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanesulfonamide → (4-{1-[(Methylsulphonyl)amino]cyclopropyl}phenyl)boronic acid

HRID 855530Notes

Reaction equation

HRID 855530 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1>CC(C)=O.C([O-])(=O)C.[NH4+]>[CH3:22][S:19]([NH:18][C:15]1([C:12]2[CH:13]=[CH:14][C:9]([B:4]([OH:5])[OH:3])=[CH:10][CH:11]=2)[CH2:17][CH2:16]1)(=[O:20])=[O:21]

Participants

4

Reactant 1

HCID 46739665N-(1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropyl)methanesulfonamide

Product 1

HCID 69516977(4-{1-[(Methylsulphonyl)amino]cyclopropyl}phenyl)boronic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 517165Ammonium AcetateSolvent

Procedure

A suspension of 810 mg (2.40 mmol) of the compound obtained in Step C and 1.95 g (9.12 mmol) of NaIO4 in a mixture of 25 ml of acetone and 7 ml of 1M aqueous ammonium acetate solution is stirred for 24 hours at ambient temperature. The solid is filtered off and rinsed with copious amounts of acetone. The filtrate is concentrated by half and the residual solution is extracted with AcOEt. The organic phase is washed (saturated NaCl solution) and dried (MgSO4) to yield, after evaporation in vacuo, the title compound.

Workup

  1. filtrationThe solid is filtered off
  2. washrinsed with copious amounts of acetone
  3. concentrationThe filtrate is concentrated by half
  4. extractionthe residual solution is extracted with AcOEt
  5. washThe organic phase is washed (saturated NaCl solution)
  6. dry with materialdried (MgSO4)
  7. customto yield
  8. customafter evaporation in vacuo

Sources & evidence

ORD record
ord-abe58cb6ef3743d2b43d60063af9e6b4
Source dataset
uspto-grants-2007_08
Patent number
US07262190B2

Reaction notes

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