تفاعل #484072

ord-e60d8837d6f94a62a50e2b3daae4e194

معادلة التفاعل

CC(C)CN([C@@H](CCCCN)C(=O)O)S(=O)(=O)c1ccc([N+](=O)[O-])cc1.Cl
Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride
Cc1ccc(S(=O)(=O)N[C@@H](CC(N)=O)C(=O)O)cc1
Nα-(4-methylbenzenesulfonyl)-L-asparagine
→
Cc1ccc(S(=O)(=O)N[C@@H](CC(N)=O)C(=O)NCCCC[C@@H](C(=O)O)N(CC(C)C)S(=O)(=O)c2ccc(N)cc2)cc1
final product
Cc1ccc(S(=O)(=O)N[C@@H](CC(N)=O)C(=O)NCCCC[C@@H](C(=O)O)N(CC(C)C)S(=O)(=O)c2ccc(N)cc2)cc1
Nα-(4-aminobenzenesulfonyl)-Nα-isobutyl-Nε-[N′α-(4-methylbenzenesulfonyl)-L-asparagyl]-L-lysine

المتفاعلات

—
Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(4-methylbenzenesulfonyl)-L-asparagyl]-L-lysine
CC(C)CN([C@@H](CCCCN)C(=O)O)S(=O)(=O)c1ccc([N+](=O)[O-])cc1.Cl
Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride
Cc1ccc(S(=O)(=O)N[C@@H](CC(N)=O)C(=O)O)cc1
Nα-(4-methylbenzenesulfonyl)-L-asparagine

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىwas prepared in step A this example
  2. 2
    أخرىPurification by HPLC

الإجراء التجريبي

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (400 mg, 1.03 mmol, example 5, step C) as described in general procedure Bc using Nα-(4-methylbenzenesulfonyl)-L-asparagine (286 mg, 1.0 mmol) which was prepared in step A this example. The final product, Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(4-methylbenzenesulfonyl)-L-asparagyl]-L-lysine was subsequently hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (185 mg, 76%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06608100B1uspto-grants-2003_08