Reaktion #353087

Reaktionsgleichung

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

Lösungsmittel

acetonitrile

THF MeOH H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter 45 min. the solution was concentrated
2. 2
   workup.ADDITIONdiluted with water
3. 3
   Waschenwashed with EtOAc
4. 4
   Extraktionextracted with EtOAc
5. 5
   TrocknenThe organic layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto give an acid which
9. 9
   EinengenThe solution was concentrated
10. 10
    workup.DISSOLUTIONdissolved in water
11. 11
    SonstigeEtOAc and the layers separated
12. 12
    TrocknenThe organic layer was dried (Na2SO4)
13. 13
    Filtrationfiltered
14. 14
    Sonstigeevaporated

Vorschrift

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.

Quelle