Reaktion #704893

ord-5b8b056833a14309ba4befa2e9b935f6

Reaktionsgleichung

C(=NC1CCCCC1)=NC1CCCCC1
DCC
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O
Boc-D-Phe-OH
O=C(OCc1ccccc1)[C@@H]1CCCN1
L-Pro-OBzl
→
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1
Boc-D-Phe-Pro-OBzl
Ausbeute 83.0%

Edukte

C(=NC1CCCCC1)=NC1CCCCC1
DCC
—
Diphenyl N-(Boc-D-Phe-Pro)amino(4-amidinophenyl)-methanephosphonate hydrochloride
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O
Boc-D-Phe-OH
O=C(OCc1ccccc1)[C@@H]1CCCN1
L-Pro-OBzl

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Diphenyl N-(Boc-D-Phe-Pro)amino(4-amidinophenyl)-methanephosphonate hydrochloride {Boc-D-Phe-L-Pro-(4-AmPhGly)P (OPh)2 }. Boc-D-Phe-OH (2.66 g, 10 mmole) and L-Pro-OBzl (2.42 g) were coupled using DCC, and Boc-D-Phe-Pro-OBzl was obtained in 83% yield; 1H NMR (CDCl3) δ 7.34 (s, 5H), 7.23 (m, 5H), 5.4 (d, 1H), 5.15 (q, 2H), 4.65 (m, 1H), 4.35 (m, 1H), 3.5 (m, 1H), 3.1-2.9 (m, 2H), 2.6 (m, 1H), 2.-1.7 (m, 4H), 1.43 (s, 9H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05952307uspto-grants-1999_09