Reaktion #336811

Reaktionsgleichung

ester

6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid methyl ester

NaOH

→

desired acid 36

6-(3-Benzyloxycarbonylaminopropionylamino)-hexanoic acid

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe compound 36 was prepared
2. 2
   SonstigeRecrystallization from MeOH

Vorschrift

The compound 36 was prepared using General Procedure A with ester 35 (3.20 g, 9.13 mmol) and an aqueous NaOH solution (1.46 g, 36.53 mmol in 40 mL of H2O) in MeOH (40 mL). Recrystallization from MeOH produced the desired acid 36 in 95% (2.92 g) yield as a white solid. 1H NMR (CDCl3): δ 7.32 (m, 5H, ArH), 6.10 (s, 1H, NH), 5.67 (s, 1H, NH), 5.04 (s, 2H, OCH2Ar), 3.45 (dt, J=6.4, 12.0 Hz, 2H, CH2NHCO), 3.21 (dt, J=6.4, 12.8 Hz, 2H, CH2NHCO), 2.40 (dt, J=6.0, 6.4 Hz, 2H, CH2CO), 2.32 (t, J=7.2 Hz, 2H, CH2CO), 1.61 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.33 (m, 2H, CH2); ESI-MS m/z 371[M+Cl]−, 359[M+Na]+, 337[M+H]+, 335[M−H]−.

Quelle