반응 #57750

반응 방정식

ethyl acetate

methyl N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate

lithium hydroxide

hydrochloric acid

→

N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine

수율 91.3%

용매

tetrahydrofuran

methanol

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The layers were separated
3. 3
   세척the organic phase was washed with water
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   기타The solid material was recrystallized from a minimum amount of boiling isopropanol
7. 7
   기타to furnish which

실험 절차

To a solution of methyl N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate (192 mg, 0.331 mmol) in tetrahydrofuran (12 mL), methanol (8 mL), water (4 mL) was added lithium hydroxide (317 mg, 13.25 mmol). After stirring for 2.5 days at room temperature hydrochloric acid (13.25 mL, 1 N solution) was added followed by ethyl acetate (80 mL). The layers were separated and the organic phase was washed with water, dried over sodium sulfate, filtered and reduced to dryness. The solid material was recrystallized from a minimum amount of boiling isopropanol to furnish which furnished 171 mg (91%) of N-[(4′-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine as a white solid. MS (ES) m/z: 564.2 (M−H), 1129.4 (2M−H).

출처