tert-butyl N-[2-(4-amino-2-methoxyphenoxy)ethyl]carbamate

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

Procedure: tert-Butyl-(4-amino-2-methoxyphenoxy)ethylcarbamate was converted to the title compound (80 mg) by acylation with 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylic acid (25 mg) following the procedure described in step C of Example 1. MS (ESI) 386 (M-Boc)+.

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

Procedure: A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq, K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward, without further purification. After dilution with H2O, the mixture was extracted 4× with CH2Cl2 The combined organic layers were washed 2× with aq, K2CO3 with brine prior to drying over Na2SO4 After removal of the solvent under vacuum the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether was carried forward, without further purification

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

Procedure: A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq, K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward, without further purification. After dilution with H2O, the mixture was extracted 4× with CH2Cl2 The combined organic layers were washed 2× with aq, K2CO3 with brine prior to drying over Na2SO4 After removal of the solvent under vacuum the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether was carried forward, without further purification

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

Procedure: A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq, K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward, without further purification. After dilution with H2O, the mixture was extracted 4× with CH2Cl2 The combined organic layers were washed 2× with aq, K2CO3 with brine prior to drying over Na2SO4 After removal of the solvent under vacuum the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether was carried forward, without further purification

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

Procedure: tert-Butyl-(4-amino-2-methoxyphenoxy)ethylcarbamate was converted to the title compound (80 mg) by acylation with 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylic acid (25 mg) following the procedure described in step C of Example 1. MS (ESI) 386 (M-Boc)+.

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

Procedure: A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° C. for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq. K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in step C of Example 6 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward without further purification. After dilution with H2O, the mixture was extracted 4× with CH2Cl2 The combined organic layers were washed 2× with aq. K2CO3 with brine prior to drying over Na2SO4 After removal of the solvent under vacuum the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether was carried forward without further purification

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

Procedure: A suspension of K2CO3 (280 mg, 2 mmol), NaI (700 mg, 5 mmol), the potassium salt of 2-methoxy-4-nitrophenol (1.37 g, 6.6 mmol), and t-butyl 2-chloroethylcarbamate (1.4 g, 8 mmol) in DMF (8 mL) was heated at 90° for 6 hr. After dilution with H2O, the mixture was extracted 4× with CH2Cl2. The combined organic layers were washed 2× with aq. K2CO3, then with brine prior to drying over Na2SO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether. Pd catalyzed reduction in ethanol as described in Example 1 yielded tert-butyl 2-(4-amino-2-methoxyphenoxy)ethylcarbamate (700 mg) as an off white solid which was carried forward without further purification. After dilution with H2O, the mixture was extracted 4× with CH2Cl2 The combined organic layers were washed 2× with aq. K2CO3 with brine prior to drying over Na2SO4 After removal of the solvent under vacuum the residue was chromatographed on silica gel using 5% EtOAc/CH2Cl2 to elute 870 mg of nitrophenyl ether was carried forward without further purification