تفاعل #81609

معادلة التفاعل

ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate

trifluoracetic acid

→

title compound

المردود 62.4%

Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]-benzenepropanoate

المردود 62.4%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىevaporated
2. 2
   أخرىThe residue was partitioned between ether and dilute sodium hydroxide solution
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with water
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىThe solvent was evaporated
7. 7
   أخرىthe residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide
8. 8
   workup.ADDITIONThe product containing fractions
9. 9
   أخرىthe solvent evaporated

الإجراء التجريبي

A solution of ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate (2.36 g) and trifluoracetic acid (5 ml) in dichloromethane (25 ml) was allowed to stand at room temperature overnight and then evaporated. The residue was partitioned between ether and dilute sodium hydroxide solution. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide. The product containing fractions were combined and the solvent evaporated to give the title compound as a gum (1.13 g), Rf 0.1 (SS 4). N.M.R. δ(CDCl3): 1.24 (3H,t), 1.48(2H,s), 2.61(2H,t), 2.73(2H,t), 2.90-2.98(4H,m), 3.93(2H,s), 4.14(2H,q), 6.88(2H,s), 6.91(1H,s), 6.96-7.03(2H,m), 7.12-7.18(2H,m).

المصدر