Reaktion #1476049

ord-dbbdc36d147e49819d2eb286520328cd

Reaktionsgleichung

Fc1c(F)c(F)c(Oc2c(F)c(F)c(F)c(F)c2F)c(F)c1F
pentafluorophenyl ether
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O
tert.butyloxycarbonyl-threonine
N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCNC(=O)OCc1ccccc1)C(=O)O
Nε -benzyloxycarbonyl-lysyl-prolyl-arginine
→
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O
desired product
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)O
TERT.BUTYLOXYCARBONYL-THREONYL-Nε -BENZYLOXYCARBONYL-LYSYL-PROLYL-ARGININE

Edukte

—
compound III
Fc1c(F)c(F)c(Oc2c(F)c(F)c(F)c(F)c2F)c(F)c1F
pentafluorophenyl ether
C[C@@H](O)[C@H](NC(=O)OC(C)(C)C)C(=O)O
tert.butyloxycarbonyl-threonine
N=C(N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CCCCNC(=O)OCc1ccccc1)C(=O)O
Nε -benzyloxycarbonyl-lysyl-prolyl-arginine

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONThen the reaction mixture is treated

Vorschrift

2.18 g (4.1 mmol) of Nε -benzyloxycarbonyl-lysyl-prolyl-arginine IV in 30 ml of water are added, under stirring, to a solution of 2.10 g (5.3 mmol) of pentafluorophenyl ether of tert.butyloxycarbonyl-threonine in 70 ml of dioxane. Then the reaction mixture is treated following the procedure described for the synthesis of compound III. The yield of the desired product--tert.butyloxycarbonyl-threonyl-Nε -benzyloxycarbonyl-lysyl-prolyl-arginine is 2.65 g (188%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04434095uspto-grants-1984_02