| 99% |
With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20℃; |
TO A] stirred solution of 4-sulfamoyl-benzoic acid methyl ester (6.01 g, 27.8 [MMOL),] 4- oxo-2-m-tolyl-pentanoic acid (6.35 g, 30.7 mmol), N, N-diisopropylethylamine (12.2 mL, 69.5 [MMOL),] and DMAP (5 mole %) in CH2Cl2 (275 mL) at rt under N2 was added [BROMO-TRIPYRROLIDINO-PHOSPHONIUM] hexafluorophosphate (PyBroP) (18.1 g, 38.9 [MMOL),] and the reaction mixture was allowed to stir overnight. The mixture was diluted with [1 M HCI] (100 mL) and [CH2CI2] (150 mL), and the layers were separated. The organic phase was washed with 1 M HCI (1 x 100 mL), 1N NaOH (1 x 100 mL) and brine [(1] x 100 mL). The organic layer was dried over [NA2SO4,] and then filtered, and the solvent was removed under reduced pressure. Purification on silica gel (0-15% EtOAc in hexane) gave 12.0 g (99%) of desired ester as a white [SOLID.'H] NMR (400 MHz, [CDCI3)] : 8.15 (d, [J=8. 6HZ,] 2H), 7.99 (d, [J=8. 6HZ,] 2H), 7.18 (t, J = 7.6 Hz, 1H), 7.10 (d, J = 7.6 Hz, 1 H), 6.87 (m, 2H), 3.97 (s, 3H), 3.93 (dd. J = 4.3 and 9.5 Hz, 1 H), 3.29 (dd. J = 9.5 and 18.1 Hz, 1 H), 2.60 (dd. J = 4.3 and 18.1 Hz, [1H),] 2.28 (s, 3H), 2.07 (s, 3H). |
| 99% |
With dmap; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 20℃; |
To astirred solution of 4-sulfamoyl-benzoic acid methyl ester (6.01 g, 27.8 mmol), 4-oxo-2-/r/-to.yi-pentanoic acid (6.35 g, 30.7 mmol), /V,A/-diisopropylethylamine(12.2 mL, 69.5 mmol), and DMAP (5 mole %) in CH2CI2 (275 ml) at rt under N2was added bromo-tripyrrolidino-phosphonium hexafluorophosphate (PyBroP)10 (18.1 g, 38.9 mmol), and the reaction mixture was allowed to stir overnight.The mixture was diluted with 1M HCI (100 ml) and CH2CI2 (150 ml), and thelayers were separated. The organic phase was washed with 1M HCI (1 x 100mL), 1N NaOH (1 x 100 ml) and brine (1 x 100 rnL). The organic layer wasdried over NajSCU, and then filtered, and the solvent was removed under15 reduced pressure. Purification on silica gel (0-15% EtOAc in hexane) gave12.0 g (99%) of desired ester as a white solid. 1H NMR (400 MHz, CDCI3):8.15 (d, J = 8.6 Hz, 2H), 7.99 (d, J = 8.6 Hz, 2H), 7.18 (t, J = 7.6 Hz, 1H), 7.10(d, J = 7.6 Hz, 1H), 6.87 (m, 2H), 3.97 (s, 3H), 3.93 (dd. J = 4.3 and 9.5 Hz,1H), 3.29 (dd. J = 9.5 and 18.1 Hz, 1H), 2.60 (dd. J = 4.3 and 18.1 Hz, 1H),20 2.28 (s, 3H), 2.07 (s, 3H). |
| 99% |
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate;dmap; In dichloromethane; at 20℃; |
B. 4-(4-Oxo-2-m-tolyl-pentanoylsulfamoyl)-benzoic acid methyl ester. To a stirred solution of 4-sulfamoyl-benzoic acid methyl ester (6.01 g, 27.8 mmol), 4-oxo-2-m-tolyl-pentanoic acid (6.35 g, 30.7 mmol), N,N-diisopropylethylamine (12.2 mL, 69.5 mmol), and DMAP (5 mole %) in CH2Cl2 (275 mL) at rt under N2 was added bromo-tripyrrolidino-phosphonium hexafluorophosphate (PyBroP) (18.1 g, 38.9 mmol), and the reaction mixture was allowed to stir overnight. The mixture was diluted with 1 M HCl (100 mL) and CH2Cl2 (150 mL), and the layers were separated. The organic phase was washed with 1 M HCl (1*100 mL), 1N NaOH (1*100 mL) and brine (1*100 mL). The organic layer was dried over Na2SO4, and then filtered, and the solvent was removed under reduced pressure. Purification on silica gel (0-15% EtOAc in hexane) gave. 12.0 g (99%) of desired ester as a white solid. 1H NMR (400 MHz, CDCl3): 8.15 (d, J=8.6 Hz, 2H), 7.99 (d, J=8.6 Hz, 2H), 7.18 (t, J=7.6 Hz, 1H), 7.10 (d, J=7.6 Hz, 1H), 6.87 (m, 2H), 3.97 (s, 3H), 3.93 (dd. J=4.3 and 9.5 Hz, 1H), 3.29 (dd. J=9.5 and 18.1 Hz, 1H), 2.60 (dd. J=4.3 and 18.1 Hz, 1H), 2.28 (s, 3H), 2.07 (s, 3H). |
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