تفاعل #52073

معادلة التفاعل

2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid ethyl ester

LiOH.H2O

LiOH.H2O

→

title compound

المردود 94.5%

2-(4-{[(3-Carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid

المردود 94.5%

المذيبات

THF

water

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was heated
2. 2
   درجة الحرارةat reflux for 24 h
3. 3
   درجة الحرارةthe reaction was heated
4. 4
   درجة الحرارةat reflux for 30 h
5. 5
   تركيزThe mixture was concentrated in vacuo and to the residue
6. 6
   workup.ADDITIONwas added THF (3 mL) and water (1.5 mL)
7. 7
   درجة الحرارةThe reaction was heated
8. 8
   درجة الحرارةat reflux for 24 h
9. 9
   workup.ADDITIONThe solution was diluted with water
10. 10
    workup.ADDITIONthe pH was adjusted to about 5 by addition of 1N HCl
11. 11
    workup.ADDITIONSodium chloride was added
12. 12
    غسيلthe aqueous solution was washed with EtOAc (3×)
13. 13
    تجفيفThe combined organic solutions were dried (MgSO4)
14. 14
    ترشيحfiltered
15. 15
    تركيزconcentrated

الإجراء التجريبي

To a solution of 2-(4-{[(3-carboxymethoxy-benzyl)-(pyridine-3-sulfonyl)-amino]-methyl}-phenyl)-2-methyl-propionic acid ethyl ester (83 mg, 0.157 mmol) in THF (10 mL) was added water (1 mL) and LiOH.H2O (66 mg, 1.58 mmol). The reaction was heated at reflux for 24 h. Additional LiOH.H2O (66 mg, 1.58 mmol) in water (2 mL) was added and the reaction was heated at reflux for 30 h. The mixture was concentrated in vacuo and to the residue was added THF (3 mL) and water (1.5 mL). The reaction was heated at reflux for 24 h and was cooled to room temperature. The solution was diluted with water and the pH was adjusted to about 5 by addition of 1N HCl. Sodium chloride was added and the aqueous solution was washed with EtOAc (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated to provide the title compound (74 mg). 1H NMR (400 MHz, CDCl3) δ 8.94 (s, 1H), 8.73 (s, 1H), 8.13 (d, 1H), 7.55 (m, 1H), 7.23 (d, 2H), 7.11 (m, 3H), 6.78 (d, 1H), 6.73 (d, 1H), 6.68 (s, 1H), 4.90 (s, 2H), 4.39 (s, 2H), 3.30 (s, 2H), 1.50 (s, 6H); MS 497 (M−1).

المصدر