تفاعل #484104

ord-4d0850293d684c58a3e6d91058252d53

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
COc1ccc(CC(=O)N[C@@H](Cc2ccccc2)C(=O)O)cc1
Nα-(4-methoxyphenylacetyl)-L-phenylalanine
→
COc1ccc(CC(=O)N[C@@H](Cc2ccccc2)C(=O)NCCCC[C@@H](C(=O)O)N(CC(C)C)S(=O)(=O)c2ccc(N)cc2)cc1
final product
COc1ccc(CC(=O)N[C@@H](Cc2ccccc2)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-methoxyphenylacetyl)-L-phenylalanyl]-L-lysine

المتفاعلات

—
Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(4-methoxyphenylacetyl)-L-phenylalanyl]-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
COc1ccc(CC(=O)N[C@@H](Cc2ccccc2)C(=O)O)cc1
Nα-(4-methoxyphenylacetyl)-L-phenylalanine

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىPurification by HPLC

الإجراء التجريبي

The title compound was prepared from Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine hydrochloride (200 mg, 0.45 mmol, example 5, step C) as described in general procedure Bc using Nα-(4-methoxyphenylacetyl)-L-phenylalanine (example 132, step A). The final product, Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-Nε-[N′α-(4-methoxyphenylacetyl)-L-phenylalanyl]-L-lysine was subsequently hydrogenolysed following the indications of general procedure E. Purification by HPLC gave the desired material (7 mg, 4%).

المصدر

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