Reaktion #343907

ord-339a528b6d524f81878ab9d910e2e5d8

Reaktionsgleichung

CC(C)CC(NC(=O)CNC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(N)=O
LHRH
O=C(O)C(F)(F)F
TFA
[Na+].[OH-]
sodium hydroxide
CC(=O)[O-].[Na+]
sodium acetate
Cc1ncc(CO)c(C=O)c1O.Cl
pyridoxal hydrochloride
→
CCNC(=O)[C@@H]1C=C2c3cccc4c3c(cn4C(C)=O)C[C@H]2N(C)C1
Ala10
CC(C)CC(NC(=O)CNC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(N)=O
LHRH

Edukte

—
VIII
CC(C)CC(NC(=O)CNC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(N)=O
LHRH
O=C(O)C(F)(F)F
TFA
[Na+].[OH-]
sodium hydroxide
CC(=O)[O-].[Na+]
sodium acetate
Cc1ncc(CO)c(C=O)c1O.Cl
pyridoxal hydrochloride
—
peptide Ac-D-Nal(2)-D-Phe(4 Cl)-D-Trp-Ser-Arg-D-Lys

Reagenzien

CC(=O)[O-].CC(=O)[O-].[Cu+2]
copper(II) acetate

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product was purified by HPLC under conditions

Vorschrift

The synthesis of peptide Ac-D-Nal(2)-D-Phe(4 Cl)-D-Trp-Ser-Arg-D-Lys[(Cu++)(POL)2 (DL-A2 pr)]-Leu-Arg-Pro-D-Ala-NH2 was performed by reacting [Ac-D-Nal(2)1, D-Phe(4Cl)2, D-Trp3, Arg5,D-Lys(DL-A2 pr)6, D-Ala10 ]LHRH (Preparation VIII, 40 mg of a TFA salt) in DMF (0.2 ml) at pH 8 (adjusted with sodium hydroxide and sodium acetate) with pyridoxal hydrochloride (Aldrich, 4 mg) then, after standing at room temperature for 1 hour, with copper(II) acetate (3 mg in 0.05 ml water). The crude product was purified by HPLC under conditions given in Example XI (system iv) to yield [Ac-D-Nal(2)1,D-Phe(4Cl)2,D-Trp3,Arg5,D-Lys[(Cu++)(POL)2 (DL-A2 pr)]6,D-Ala10 ]LHRH (40 mg) with HPLC retention time of 6.3 min.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05258492uspto-grants-1993_11