Reaction #336809

Reaction equation

diester

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

NaOH

→

diacid

3-[2-(3-Benzyloxycarbonylaminopropionylamino)-3-(2-carboxy-ethoxy)propoxy]-propionic acid

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe compound 8 was prepared

Procedure

The compound 8 was prepared using General Procedure A with diester 29 (1.32 g, 2.66 mmol) and an aqueous NaOH solution (0.85 g, 21.29 mmol in 10 mL of H2O) in methanol (10 mL). The desired diacid (8) was obtained in 96% (1.12 g) yield as a colorless syrup. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.59 (s, 1H, NH), 5.54 (s, 1H, NH), 5.08 (s, 2H, OCH2Ar), 4.18 (m, 1H, CH), 3.69 (m, 4H, CH2O), 3.56 (m, 2H, CH2O), 3.45 (m, 4H, CH2NHCO and CH2O), 2.55 (m, 4H, CH2O), 2.43 (m, 2H, CH2CO); ESI-MS m/z 475[M+Cl]−; 463[M+Na]+, 441 [M+H]+, 439[M−H]−.

Source