Réaction #829568

Équation de réaction

β-alanine benzyl ester tosylate

Boc-L-phenylalanine

H2O

DIPEA

WSCDI

→

Boc-L-phenylalanyl-β-alanine, benzyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONtreated with HoBt
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued overnight
4. 4
   Autrethe solvent removed
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (30 mL)
6. 6
   Lavagewashed with water, 10% sodium bicarbonate solution
7. 7
   SéchageThe organic layer was dried (MgSO4)
8. 8
   Autreevaporated to a white solid

Mode opératoire

Boc-L-phenylalanine (1.32 g, 5.00 mmol) was dissolved in dichloromethane (50 mL) and treated with HoBt.H2O (1.53 g, 2.00 mmol) followed by WSCDI (water soluble carbodiimide) (1.00 g, 5.24 mmol). After stirring for 40 minutes, β-alanine benzyl ester tosylate (1.85 g, 5.27 mmol) was added, followed by DIPEA (diisopropylethylamine) (1.29 g, 10 mmol). Stirring was continued overnight, then the solvent removed. The residue was dissolved in ethyl acetate (30 mL) and washed with water, 10% sodium bicarbonate solution, then 10% citric acid solution. The organic layer was dried (MgSO4) and evaporated to a white solid--a single component by TLC, 1.74 g, 82% of (32). NMR (CDCl3) δ 1.41 (9H, s), 2.47 (2H, m), 3.01 (2H, m), 3.45 (2H, m), 4.25 (1H, br.q), 5.00 (1H, br.s), 5.07 (2H, s), 6.21 (1H, br.t), 7.15-7.38 (10H, m).

Source