tert-butyl 3-(phenylamino)propanoate

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

Procedure: To a solution of the title compound of Example B (29.37 g, 0.133 mol) and di-tert-butyl oxalate (26.90 g, 0.133 mol) in dry THF (350 ml) was added potassium tert-butoxide (29.84 g, 0.266 mol) and the resulting solution was heated under reflux for 24 h. The mixture was then cooled and the solvent removed in vacuo. The resulting solid was suspended in CH2Cl2 and 1N aqueous HCl was added. The resulting suspension was filtered and the organic filtrate was dried over MgSO4 and concentrated in vacuo. The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2 to give the title compound (19.06 g, 52%) as a solid. Anal calcd for C15H17NO4 : C, 65.44; H, 6.22; N, 5.09. Found: C, 65.05; H, 6.33; N, 4.86. MS M+1 calcd for C15H17NO4 276, found 276. the resulting solution was heated under reflux for 24 h The mixture was then cooled the solvent removed in vacuo 1N aqueous HCl was added The resulting suspension was filtered the organic filtrate was dried over MgSO4 concentrated in vacuo The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2

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

Procedure: To a solution of aniline (27.9 g, 0.30 mol) and tert-butyl acrylate (38.4 g, 0.30 mol) in dry benzene (500 ml) was added tin tetrachloride (2 ml) and the resulting solution was heated under reflux for 18 8 h. The resulting suspension was filtered and the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane to give the title compound (22.53 g, 34%) as an oil. 1H NMR (300 MHz, CDCl3) δ7.12 (2H, t), 6.71 (1H, m), 6.62 (2H, d), 3.40 (2H, t), 2.54 (2H, t), 1.44 (9H, s). the resulting solution was heated under reflux for 18 8 h The resulting suspension was filtered the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane

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

Procedure: To a solution of the title compound of Example B (29.37 g, 0.133 mol) and di-tert-butyl oxalate (26.90 g, 0.133 mol) in dry THF (350 ml) was added potassium tert-butoxide (29.84 g, 0.266 mol) and the resulting solution was heated under reflux for 24 h. The mixture was then cooled and the solvent removed in vacuo. The resulting solid was suspended in CH2Cl2 and 1N aqueous HCl was added. The resulting suspension was filtered and the organic filtrate was dried over MgSO4 and concentrated in vacuo. The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2 to give the title compound (19.06 g, 52%) as a solid. Anal calcd for C15H17NO4 : C, 65.44; H, 6.22; N, 5.09. Found: C, 65.05; H, 6.33; N, 4.86. MS M+1 calcd for C15H17NO4 276, found 276. the resulting solution was heated under reflux for 24 h The mixture was then cooled the solvent removed in vacuo 1N aqueous HCl was added The resulting suspension was filtered the organic filtrate was dried over MgSO4 concentrated in vacuo The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2

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

Procedure: To a solution of the title compound of Example B (29.37 g, 0.133 mol) and di-tert-butyl oxalate (26.90 g, 0.133 mol) in dry THF (350 ml) was added potassium tert-butoxide (29.84 g, 0.266 mol) and the resulting solution was heated under reflux for 24 h. The mixture was then cooled and the solvent removed in vacuo. The resulting solid was suspended in CH2Cl2 and 1N aqueous HCl was added. The resulting suspension was filtered and the organic filtrate was dried over MgSO4 and concentrated in vacuo. The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2 to give the title compound (19.06 g, 52%) as a solid. Anal calcd for C15H17NO4 : C, 65.44; H, 6.22; N, 5.09. Found: C, 65.05; H, 6.33; N, 4.86. MS M+1 calcd for C15H17NO4 276, found 276. the resulting solution was heated under reflux for 24 h The mixture was then cooled the solvent removed in vacuo 1N aqueous HCl was added The resulting suspension was filtered the organic filtrate was dried over MgSO4 concentrated in vacuo The residue was then chromatographed on silica gel eluting with 1/1/98 HOAc/EtOH/CH2Cl2

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

Procedure: To a solution of aniline (27.9 g, 0.30 mol) and tert-butyl acrylate (38.4 g, 0.30 mol) in dry benzene (500 ml) was added tin tetrachloride (2 ml) and the resulting solution was heated under reflux for 18 h. The resulting suspension was filtered and the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane to give the title compound (22.53 g, 34%) as an oil. 1H NMR (300 MHz, CDCl3) δ7.12 (2H, t), 6.71 (1H, m), 6.62 (2H, d), 3.40 (2H, t), 2 54 (2H, t), 1.44 (9H, s). the resulting solution was heated under reflux for 18 h The resulting suspension was filtered the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane

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

Procedure: To a solution of aniline (27.9 g, 0.30 mol) and tert-butyl acrylate (38.4 g, 0.30 mol) in dry benzene (500 ml) was added tin tetrachloride (2 ml) and the resulting solution was heated under reflux for 18 8 h. The resulting suspension was filtered and the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane to give the title compound (22.53 g, 34%) as an oil. 1H NMR (300 MHz, CDCl3) δ7.12 (2H, t), 6.71 (1H, m), 6.62 (2H, d), 3.40 (2H, t), 2.54 (2H, t), 1.44 (9H, s). the resulting solution was heated under reflux for 18 8 h The resulting suspension was filtered the filtrate was concentrated in vacuo giving a residue which was chromatographed on silica gel eluting with 25/75 ethyl acetate/hexane