3-hydroxy-N,N-dimethylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DIAD (48 uL, 0.24 mmol) was added dropwise to a RT solution of 3-hydroxy-N,N,-dimethyl-benzenesulfonamide (0.040 g, 0.2 mmol), 3-[(3-chloro-2-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol (0.088 g, 0.2 mmol) and triphenylphosphine (0.063 g, 0.24 mmol). The mixture was stirred for 48 at rt than was concentrated and purified by reverse phase HPLC to provide a solid which was dissolved in CH2Cl2 and treated with excess 4M HCl in diethyl ether. The mixture was concentrated to provide 35 mg (25%) of the title compound. MS (ESI) 632 (M+H+). than was concentrated purified by reverse phase HPLC to provide a solid which The mixture was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of BBr3 (1 M in CH2Cl2, 2.0 mL, 2.0 mmol) was added dropwise to a −78° C. solution of 3-methoxy-N,N,-dimethyl-benzenesulfonamide (0.15 g, 0.7 mmol) in CH2Cl2 (2 mL). The mixture was warmed to rt and stirred for 2 h, then cooled to 0° C. and quenched with saturated NaCO3. The aqueous phase was neutralized with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to give an oil which was directly in the next step. MS (ESI) 202 (M+H+). cooled to 0° C. quenched with saturated NaCO3 extracted with EtOAc The organic extracts were washed with brine dried (MgSO4) filtered concentrated to give an oil which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of BBr3 (1 M in CH2Cl2, 2.0 mL, 2.0 mmol) was added dropwise to a −78° C. solution of 3-methoxy-N,N,-dimethyl-benzenesulfonamide (0.15 g, 0.7 mmol) in CH2Cl2 (2 mL). The mixture was warmed to rt and stirred for 2 h, then cooled to 0° C. and quenched with saturated NaCO3. The aqueous phase was neutralized with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to give an oil which was directly in the next step. MS (ESI) 202 (M+H+). cooled to 0° C. quenched with saturated NaCO3 extracted with EtOAc The organic extracts were washed with brine dried (MgSO4) filtered concentrated to give an oil which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DIAD (48 uL, 0.24 mmol) was added dropwise to a RT solution of 3-hydroxy-N,N,-dimethyl-benzenesulfonamide (0.040 g, 0.2 mmol), 3-[(3-chloro-2-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol (0.088 g, 0.2 mmol) and triphenylphosphine (0.063 g, 0.24 mmol). The mixture was stirred for 48 at rt than was concentrated and purified by reverse phase HPLC to provide a solid which was dissolved in CH2Cl2 and treated with excess 4M HCl in diethyl ether. The mixture was concentrated to provide 35 mg (25%) of the title compound. MS (ESI) 632 (M+H+). than was concentrated purified by reverse phase HPLC to provide a solid which The mixture was concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of BBr3 (1 M in CH2Cl2, 2.0 mL, 2.0 mmol) was added dropwise to a −78° C. solution of 3-methoxy-N,N,-dimethyl-benzenesulfonamide (0.15 g, 0.7 mmol) in CH2Cl2 (2 mL). The mixture was warmed to rt and stirred for 2 h, then cooled to 0° C. and quenched with saturated NaCO3. The aqueous phase was neutralized with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to give an oil which was directly in the next step. MS (ESI) 202 (M+H+). cooled to 0° C. quenched with saturated NaCO3 extracted with EtOAc The organic extracts were washed with brine dried (MgSO4) filtered concentrated to give an oil which