Reaktion #2301453

Reaktionsgleichung

H-Asp (OtBu)-OtBu hydrochloride

2-(3-tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester

HOBt

PYBOP

DIPEA

→

title compound

Ausbeute 86.4%

2-(2-tert-Butoxycarbonylmethyl-5-tritylsulfanyl-pentanoylamino)-succinic acid di-tert-butyl ester

Ausbeute 86.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Vorschrift

To H-Asp (OtBu)-OtBu hydrochloride salt (28 mg, 0.10 mmol) in dry DMF (2 mL) was sequentially added at room temperature 2-(3-tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester (50 mg, 0.10 mmol), HOBt (14 mg, 0.10 mmol), PYBOP (56 mg, 0.11 mmol) and DIPEA (37 μL, 0.20 mmol). The usual aqueous work up yielded the title compound (62 mg, 86%) as a colorless residue: 1H NMR (CDCl3, 400 MHz) δ 7.41–7.38 (m, 6H), 7.29–7.25 (m, 6H), 6.60–6.57 (m, 1H), 4.68–4.56 (m, 1H), 3.18–3.14 (m, 2H), 2.89–2.80 (m, 1H), 2.74–2.52 (m, 2H), 2.43–2.36 (m, 1H), 2.32–2.19 (m, 1H), 2.12–2.07 (m, 2H), 1.83–1.80 (m, 2H), 1.60–1.53 (m, 1H), 1.45–1.40 (m, 27H); 13C (DEPT) (CDCl3, 100 MHz) δ 129.4, 127.7, 126.4, 49.0, 48.7, 46.1, 42.5, 37.8, 37.6, 37.2, 31.6, 31.5, 29.6, 27.9, 27.8, 27.7, 26.3, 26.2, 26.0.

Quelle