Tert-Butanesulfinamide → HCID 66637154, compound

HRID 2108838Notes

Reaction equation

HRID 2108838 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][C:15]([S:18]([NH2:20])=[O:19])([CH3:17])[CH3:16].[B-].[Na+]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:20][S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 3382465Tert-ButanesulfinamideHCID 115863891-(4-amino-3-nitrophenyl)ethanoneHCID 22959485Vertellus

Product 1

HCID 66637154HCID 66637154, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(4-amino-3-nitrophenyl)ethanone (500 mg, 2.78 mmol, J. Med. Chem. 1998, 41, 1777-1788), 2-methylpropane-2-sulfinamide (674 mg, 5.56 mmol) in THF (25 mL) was added titanium(IV) ethoxide (1.75 ml, 8.34 mmol) at room temperature. The mixture was stirred at 80° C. for 24 hours. After cooling to room temperature, sodium borohydrate (316 mg, 8.34 mmol) was added to the mixture at room temperature. The mixture was stirred at room temperature for 14 hours. The mixture was quenched with MeOH (6 ml), poured into saturated sodium hydrogencarbonate aqueous solution (20 mL), extracted with EtOAc (150 mL×2). The combined organic layer was washed with brine (50 mL), dried over sodium sulfate and concentrated. The residue was chromatgraphed on a column of silica gel with hexane-EtOAc (1:2) as an eluent to afford 675 mg (85%) of title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.11 (9H, s), 1.37 (3H, d, J=6.6 Hz), 4.33-4.24 (1H, m), 5.64 (1H, d, J=6.6 Hz), 6.99 (1H, d, J=8.8 Hz), 7.40 (2H, s), 7.45 (1H, d, J=8.8 Hz), 7.97 (1H, s). MS (ESI) m/z 286 (M+H)+, 284 (M−H)−.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred at room temperature for 14 hours
  3. customThe mixture was quenched with MeOH (6 ml)
  4. additionpoured into saturated sodium hydrogencarbonate aqueous solution (20 mL)
  5. extractionextracted with EtOAc (150 mL×2)
  6. washThe combined organic layer was washed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-92d28ca86cc348f9bdd2e7181f485f93
Source dataset
uspto-grants-2009_04
Patent number
US07514457B2

Reaction notes

Loading…