Réaction #336808

Équation de réaction

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide

ester hydrochloride salt

3-[2-Amino-3-(2-ethoxycarbonylethoxy)propoxy]-propionic acid ethyl ester HCl salt

N-Cbz-β-alanine

Et3N

→

desired product ( 29 )

Rendement 92.0%

3-[2-(3-Benzyloxycarbonylaminopropionylamino)-3-(2-ethoxycarbonylethoxy)-propoxy]-propionic acid ethyl ester

Rendement 92.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe compound 29 was prepared
2. 2
   AutrePurification by flash column chromatography (on silica gel, EtOAc:n-hexane=3:1)

Mode opératoire

The compound 29 was prepared using General Procedure B with the ester hydrochloride salt (28) (1.53 g, 5.26 mmol), N-Cbz-β-alanine (1.41 g, 6.31 mmol), 1-hydrobenzotriazole (HOBt) (0.99 g, 7.36 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (1.41 g, 7.36 mmol) and Et3N (1.02 mL, 7.36 mmol) in CH2Cl2 (30 mL). Purification by flash column chromatography (on silica gel, EtOAc:n-hexane=3:1) afforded 2.39 g (92%) of the desired product (29) as a colorless liquid. 1H NMR (CDCl3): δ 7.33 (m, 5H, ArH), 6.33 (d, J=8.0 Hz, 1H, NH), 5.57 (s, 1H, NM, 5.08 (s, 2H, OCH2Ar), 4.18 (m, 1H, CH), 4.13 (q, J=7.2 Hz, 4H, CH2O), 3.70 (m, 4H, CH2O), 3.56 (m, 2H, CH2O), 3.48 (d, J=6.0, 12.0 Hz, 2H, CH2NHCO), 3.40 (m, 2H, CH2O), 2.53 (m, 4H, CH2CO), 2.42 (t, J=6.0 Hz, 2H, CH2CO), 1.25 (t, J=7.2 Hz, 6H, CH3).

Source