反応 #57629

反応方程式

(S)-2-{4′-[(4-ethoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

THF

LiOH

→

(S)-3-methyl-2-{4′-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid

収率 86.0%

反応条件

後処理

1. 1
   その他The solvents were removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved in 5 mL of water
3. 3
   ろ過the resulting suspension was filtered
4. 4
   その他The solid product was dried under vacuum

実験手順

To 100 mg of (S)-2-{4′-[(4-ethoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester dissolved in 1 mL of THF was added 3 mL of LiOH solution (3.6 g LiOH/50 mL MeOH/50 mL H2O). The mixture was stirred at room temperature for 4 days. The solvents were removed under vacuum and the residue was dissolved in 5 mL of water. The solution was acidified and the resulting suspension was filtered. The solid product was dried under vacuum to give 84 mg (86% yield) of (S)-3-methyl-2-{4′-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid, obtained as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.8 (dd, J=12.9, 6.8 Hz, 6 H) 1.1 (t, J=7.3 Hz, 3 H) 1.8 (m, 2 H) 2.0 (m, 1 H) 2.8 (s, 3 H) 3.6 (dd, J=9.1, 6.1 Hz, 1 H) 4.1 (t, J=6.2 Hz, 2 H) 6.8 (d, J=8.1 Hz, 1 H) 7.2 (d, J=8.1 Hz, 1 H) 7.4 (t, J=8.2 Hz, 1 H) 7.8 (d, J=8.8 Hz, 2 H) 7.9 (m, 4 H) 8.0 (d, J=8.8 Hz, 2 H) 8.1 (d, J=9.3 Hz, 1 H) 10.5 (s, 1 H) 12.6 (s, 1 H).

出典