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

HRID 891169Notes

Reaction equation

HRID 891169 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 (step 1, 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 h. The mixture was poured into ice-2 M HCl (200 mL) and extracted with ethyl acetate, (300 mL), and the organic fraction was dried (MgSO4). After removal of solvent, the residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (20:1) 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 11.95 (1H, br.s), 7.97 (1H, s), 7.75-7.67 (2H, m), 7.40 (2H, d, J=8.6 Hz), 7.13 (2H, d, J=7.7 Hz), 4.18 (2H, t, J=6.6 Hz), 2.81 (2H, t, J=6.6 Hz), 2.40 (3H, s).

Workup

  1. extractionextracted with ethyl acetate, (300 mL)
  2. dry with materialthe organic fraction was dried (MgSO4)
  3. customAfter removal of solvent
  4. customthe residue was purified by silica-gel column chromatography
  5. washeluting with dichloromethane/methanol (20:1)

Sources & evidence

ORD record
ord-8fce211998de4736b7ad53ef999629c8
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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