تفاعل #11948

ord-f1bdec720c284c5a909cb7ee228ab562

معادلة التفاعل

O=C(O)C(F)(F)F
trifluoroacetic acid
CSc1ccccc1
thioanisole
Cc1cccc(O)c1
m-cresol
CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)s1
compound
CC(C)(C)OC(=O)N(Cc1ccccn1)Cc1ccc(C(=O)N[C@@H](CCCNC(=O)OCc2ccccc2)C(=O)O)s1
Nα-(5-(N-Boc-N-2-picolylaminomethyl)thiophene-2-carbonyl)-Nδ-Cbz-L-ornithine
NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O
title compound
المردود 53.3%
NCCC[C@H](NC(=O)c1ccc(CNCc2ccccn2)s1)C(=O)O
Nα-(5-(N-2-picolylaminomethyl)thiophene-2-carbonyl)-L-ornithine
المردود 53.3%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزthe reaction solution was concentrated
  2. 2
    workup.ADDITIONMethanol was added to the residue
  3. 3
    غسيلthe mixture was washed with hexane
  4. 4
    تركيزThe methanol layer was concentrated
  5. 5
    أخرىthe residue was crude-purified by silica gel column chromatography (3 g, chloroform/methanol/water=7/3/0.5)

الإجراء التجريبي

A mixed solution of trifluoroacetic acid (1.4 ml), thioanisole (0.36 ml), and m-cresol (0.32 ml) was added to the compound obtained in Example 14-3 (56.2 mg). After 1.5 hours, the reaction solution was concentrated. Methanol was added to the residue and the mixture was washed with hexane. The methanol layer was concentrated and the residue was crude-purified by silica gel column chromatography (3 g, chloroform/methanol/water=7/3/0.5) to obtain the title compound (18.2 mg) as colorless syrup.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07098215B2uspto-grants-2006_08