تفاعل #353087

معادلة التفاعل

31-1

3-[(N-Boc-Piperidin-4-ylmethyl)aminocarbonyl]benzoyl-2(S)-3-pyridylsulfonylamino-β-alanine methyl ester

LiOH·H2O

glycine benzyl ester·HCl

N-methylmorpholine

BOP reagent

→

31-2

3-[(N-Boc-Piperidin-4-ylmethyl)aminocarbonyl]benzoyl-2(S)-3-pyridylsulfonylamino-β-alanyl-glycine benzyl ester

المذيبات

acetonitrile

THF MeOH H2O

ظروف التفاعل

المعالجة

1. 1
   تركيزAfter 45 min. the solution was concentrated
2. 2
   workup.ADDITIONdiluted with water
3. 3
   غسيلwashed with EtOAc
4. 4
   استخلاصextracted with EtOAc
5. 5
   تجفيفThe organic layer was dried (Na2SO4)
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated
8. 8
   أخرىto give an acid which
9. 9
   تركيزThe solution was concentrated
10. 10
    workup.DISSOLUTIONdissolved in water
11. 11
    أخرىEtOAc and the layers separated
12. 12
    تجفيفThe organic layer was dried (Na2SO4)
13. 13
    ترشيحfiltered
14. 14
    أخرىevaporated

الإجراء التجريبي

A solution of 31-1 (0.75 g, 1.5 mmol) in 1:1:1 THF/MeOH/H2O (15 mL) was treated with LiOH·H2O (0.37 g, 8.8 mmol). After 45 min. the solution was concentrated, diluted with water, washed with EtOAc. The aqueous layer was acidified to pH 2-3 with 10% KHSO4 and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and evaporated to give an acid which was dissolved in acetonitrile (3 mL) and treated with glycine benzyl ester·HCl (0.1 g, 0.5 mmol), N-methylmorpholine (0.11 mL, 0.98 mmol), and BOP reagent (0.26 g, 0.58 mmol) for 24 h. The solution was concentrated, dissolved in water and EtOAc and the layers separated. The organic layer was dried (Na2SO4), filtered and evaporated. Column chromatography (SiO2, 70% acetone/hexanes) gave 31-2 as a white solid.

المصدر