反応 #52067

反応方程式

Et3N

(3-aminomethyl-phenoxy)-acetic acid tert-butyl ester

pyridine-3-sulfonyl chloride hydrochloride

→

title compound

収率 78.1%

{3-[(Pyridine-3-sulfonylamino)-methyl]-phenoxy}-acetic acid tert-butyl ester

収率 78.1%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他was quenched with a 1:1 solution of water and saturated aqueous NaHCO3
2. 2
   洗浄The aqueous solution was washed with CH2Cl2 (3×)
3. 3
   乾燥The combined organic solutions were dried (MgSO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated

実験手順

To a solution of (3-aminomethyl-phenoxy)-acetic acid tert-butyl ester (296 mg, 1.25 mmol) in CH2Cl2 at 0° C. was added pyridine-3-sulfonyl chloride hydrochloride (279 mg, 1.31 mmol) followed by Et3N (0.36 mL, 2.6 mmol). The reaction was stirred at room temperature for 24 h and was quenched with a 1:1 solution of water and saturated aqueous NaHCO3. The aqueous solution was washed with CH2Cl2 (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (1:1 hexanes:EtOAc) provided the title compound as a white solid (369.5 mg). 1H NMR (400 MHz, CDCl3) δ 9.04 (s, 1H), 8.75 (m, 1H), 8.09 (d, 1H), 7.44 (m, 1H), 7.15 (m, 1H), 6.76 (m, 3H), 5.23 (bs, 1H), 4.44 (s, 2H), 4.16 (d, 2H), 1.47 (s, 9H); MS 379 (M+1).

出典