phthalaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 2-[1-(3-Ethoxy-4-methoxyphenyl)-2-(N,N-dimethylaminosulfonyl)ethyl]isoindolin-1-one was prepared by the procedure of Example 3 from 1-(3-ethoxy-4-methoxyphenyl)-2-(N,N-dimethylaminosulfonyl)ethylamine (150 mg, 0.49 mmol) and 1,2-phthalic dicarboxaldehyde (67 mg, 0.49 mmol) in acetic acid (2 mL). The product was obtained as a solid (142 mg, 69% yield): mp, 165.0-167.0° C.; 1H NMR (CDCl3) δ 1.45 (t, J=7 Hz, 3H, CH3), 2.86 (s, 6H, N(CH3)2), 3.58 (dd, J=4.7, 14.4 Hz, 1H, CHH), 3.86 (s, 3H, CH3), 4.08 (q, J=7 Hz, 2H, CH2), 4.30 (d, J=16.5 Hz, 1H, NCHH), 4.33 (dd, J=9, 14.4 Hz, 1H, CHH), 4.49 (d, J=16.5 Hz, 1H, NCHH), 5.60 (dd, J=4.7, 9.5 Hz, 1H, NCH), 6.83 (d, J=8.3 Hz, 1H, Ar), 6.98 (dd, J=2, 8.3 Hz, 1H, Ar), 7.06 (d, J=2 Hz, 1H, Ar), 7.37-7.56 (m, 3H, Ar), 7.84 (d, J=7 Hz, 1H, Ar), 13C NMR (CDCl3) δ 14.69, 37.31, 48.64, 49.73, 52.91, 52.95, 64.54, 111.31, 112.46, 119.29, 122.76, 123.72, 128.03, 130.67, 131.55, 132.75, 141.26, 148.73, 149.39, 168.63; Anal Calcd for C21H26NO5S: C, 60.27; H, 6.26; N, 6.69. Found: C, 60.04; H, 6,10: N, 6.62.

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

Procedure: A stirred mixture 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (100 mg, 0.37 mmol) and 1,2-phthalic dicarboxaldehyde (49 mg, 0.37 mmol) in acetic acid (2 mL) was heated to reflux for 15 min. Removal of solvent in vacuo and chromatography gave an oil which was stirred with ether (2 mL). The resulting suspension was filtered to yield 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]isoindolin-1-one as a light yellow solid (100 mg, 70% yield): mp, 130.0-134.0° C.; 1H NMR (CDCl3) δ 1.45 (t, J s=7 Hz, 3H, CH3), 2.96 (s, 3H, CH3), 3.70 (dd, J=4.5, 14.7, Hz, 1H, CHH), 3.86 (s, 3H, CH3), 4.07 (q, J=6.9 Hz, 2H, CH2), 4.25 (d, J=16.5 Hz, 1H, CHH), 4.31 (dd, J=10.3, 14.5 Hz, 1H, CHH), 4.46 (d, J=16 HZ, 1H, CHH), 5.71 (dd, J=4.5, 10.3 Hz, 1H, NCH), 6.84-7.01 (m, 3H, Ar), 7.38-7.56 (m, 3H, Ar), 7.85 (d, J=6.9 Hz, 1H, Ar); 13C NMR (CDCl3) δ 14.65, 41.33, 46.27, 52.33, 55.95, 56.00, 65.56, 111.45, 112.28, 119.30, 122.85, 123.85, 128.13, 129.89, 131.80, 132.27, 141.26, 148.88, 149.62, 169.09; Anal Calcd for C20H23NO5S: C, 61.68; H, 5.95; N, 3.60. Found: C, 61.68, H, 6.06; N, 3.62. to reflux for 15 min Removal of solvent in vacuo and chromatography gave an oil which The resulting suspension was filtered

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

Procedure: From o-phthalaldehyde and 2-(triphenylphosphoranylidene)-butanoic acid 1,1-dimethylethyl ester.

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

Procedure: From o-phthalaldehyde and 2-(triphenylphosphoranylidene)-pentanoic acid ethyl ester.

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

Procedure: From 2-(triphenylphosphoranylidene)propanoic acid 1,1-dimethylethyl ester and ortho phthalaldehyde

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.32 g (0.76 mmol) of 2-(2R)-(4-chlorobiphenylsulfonylamino)-5-amino-pentanoic acid hydrochloride is dissolved in 30 ml of glacial acetic acid with 0.186 g (1.35 mmol) of phthalaldehyde and stirred at 100° C. for 3 hours. The solution is cooled to 0° C., and the precipitate which is deposited is filtered off with suction and chromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2). The solution is cooled to 0° C. the precipitate which is deposited is filtered off with suction chromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.32 g (0.76 mmol) of 2-(2R)-(4-chlorobiphenylsulfonylamino)-5-amino-pentanoic acid hydrochloride is dissolved in 30 ml of glacial acetic acid with 0.186 g (1.35 mmol) of phthalaldehyde and stirred at 100° C. for 3 hours. The solution is cooled to 0° C., and the precipitate which is deposited is filtered off with suction and chromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2). The solution is cooled to 0° C. the precipitate which is deposited is filtered off with suction chromatographed on a silica gel column (eluent: ethyl acetate/petroleum ether/glacial acetic acid 10/10/2)