p-Toluenesulfonyl isocyanate → 4-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

HRID 967806Notes

Reaction equation

HRID 967806 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1.[C:13]1([CH3:25])[CH:18]=[CH:17][C:16]([S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[CH3:25][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]([O:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([B:10]([OH:12])[OH:11])=[CH:8][CH:9]=2)=[O:24])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 77703p-Toluenesulfonyl isocyanateHCID 101762864-(2-Hydroxyethyl)phenylboronic acid

Product 1

HCID 218765304-{2-[({[(4-Methylphenyl)sulfonyl]amino]carbonyl)oxy]ethyl}phenylboronic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(2-Hydroxyethyl)phenylboronic acid (1.00 g, 6.02 mmol) was treated with pyridine (90 mL) and p-toluenesulfonylisocyanate (1.01 mL, 6.63 mmol) at room temperature for 2 hours. The mixture was poured into ice-2M HCl (200 mL) and extracted with ethyl acetate, and the organic fraction was dried (MgSO4). After removal of solvent, the residue was purified flash column chromatography on silica gel eluting with dichloromethane/methanol to give 2.20 g (quant.) of the title compound as white solids: MS (ESI) m/z 381 [M+NH4]+, 362 [M−H]−, 1H-NMR (DMSO-d6) δ 2.40 (3H, s), 2.81 (2H, t, J=6.6 Hz), 4.18 (2H, t, J=6.6 Hz), 7.13 (2H, d, J=7.7 Hz), 7.40 (2H, d, J=8.6 Hz), 7.67-7.75 (2H, m), 7.97 (1H, s), 11.95 (1H, br).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic fraction was dried (MgSO4)
  3. customAfter removal of solvent
  4. customthe residue was purified flash column chromatography on silica gel eluting with dichloromethane/methanol

Sources & evidence

ORD record
ord-86e73d1f76c74e6bbfc8b64b13e983d9
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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