반응 #829568

반응 방정식

β-alanine benzyl ester tosylate

Boc-L-phenylalanine

H2O

DIPEA

WSCDI

→

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

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

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