Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
18.8.22.11.1.1 Method 1: From Guanidines

DOI: 10.1055/sos-SD-118-00076

Kubik, S.Science of Synthesis Knowledge Updates, (20133291.

Reaction of the guanidine group in the side chain of an arginine residue with N-succin­imidyl N-methylcarbamate introduces an N-carbamimidoylurea residue into a cyclopeptide side chain.[‌307‌,‌308‌] N,N-Disubstituted N′-aminocarbonyl(benzotriazolyl)carboximid­amides 66 (Scheme 119) yield N-carbamimidoylureas upon reaction with amines, albeit only in low yields (up to 43%).[‌309‌] The major products, sometimes the only products, are di- and trisubstituted ureas. More efficient reagents for the conversion of amines into N-carbamimidoylureas are N-(tert-butoxycarbonyl)-N′-[(4-methoxybenzyl)(methyl)carbamoyl]-1H-pyrazole-1-carboximidamide (67), 1,2-bis(tert-butoxycarbonyl)guanidine (68), and 1,2,3-tris(tert-butoxycarbonyl)guanidine (69).

Meeeee 888 Meeeeeee eee eee Meeeeeeee ee M-Meeeeeeeeeeeeeeeee eeee Meeeee

Meeeeeee 88 eee eeeeeeeee ee eeeeeee eeeeeeeeee ee eeeee eeeeee ee eee eeee eeeeee ee eeeee eeeee eeee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeee eeeeee. Mee eeeeeeeee eeeeeeee eeeeeeee ee eeeeeeeee ee e eeeeeee ee eeeeeeeeeeee eeeeeeeeee e eeeeeeeeeee eeee eeeee eeeee eeeee (ee, eee eeeeeee, e eeeeee ee ee eeeeeeeee eeeeeee) eeee 88 ee eeee eeeeeeeeeee ee eee eeeeeeee ee M,M-eeeeeeeeeeeeeeeeeeeee, eeeeeeee ee eeeeeeee ee eee eeee-eeeeeeeeeeeeee eee 8-eeeeeeeeeeeee eeeeee.[‌888‌,‌888‌]

8,8-Mee(eeee-eeeeeeeeeeeeee)eeeeeeeee (88) eeeeee eeee eeeeeee eeeeeeeee eeeeee ee eeeeeeee eeeeeeeeeee ee eeeeeee eee eeeeeeeeeeeee M-eeeeeeeeeeeeeeeeee 88 (Meeeee 888).[‌888‌] Meee eeeeeeee ee eeeeeeee ee eeeeeee eeeeeee eeeeeeeee ee ee eeeeeeeeee ee eeeeeeeeeee ee eeee-eeeee eeeeeee eeeeeeee ee eeeeeeee ee eee eeeee ee eeee eee eeee.

Meeeee 888 M-Meeeeeeeeeeeeeeee Meeeeeeee eeee 8,8-Mee(eeee-eeeeeeeeeeeeee)eeeeeeeee eee e Meeeeee Meeee[‌888‌]

Me 8,8,8-eeee(eeee-eeeeeeeeeeeeee)eeeeeeeee (88) ee eeee, eeeeeeee eeee 8 eeeeeeeeee ee ee eeeee eeeeeeeee eeeee ee ee M-eeeeeeeeeee eeeeeeeee (Meeeee 888). Mee eeeeeeeeeeeee ee­eeeeeeeeeee M-eeeeeeeeeeeeeeeeee eee eeee ee eeeeeeee ee eee eeeeeeee ee ee eeeeee ee eeeee (8–8 eeeeeeeeeee).[‌888‌] Meeee eeeeeeeee eeeeeeeeee, eeeeee ee ee ee 88% eee ee eeeeeeee. Mee eeeeeeee ee, eeeeeee, eeeeeeeeee ee eeeeeeeee eeeeee.

Meeeee 888 M-Meeeeeeeeeeeeeeee Meeeeeeee eeee 8,8,8-Meee(eeee-eeeeeeeeeeeeee)eeeeeeeee eee e Meeeeee Meeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8-[M′-(eeee-eeeeeeeeeeeeee)eeeeeeeeeeeee]eeee (88, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8,8-eee(eeee-eeeeeeeeeeeeee)eeeeeeeee (88; 8.8 e, 8 eeee) eee MeMM8 (8.8 eM, 88 eeee) ee eeeee MMM (88 eM) eee eeeeeeee eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8) ee eeeee e eeeeeeeee eeeeee eeeeeeee eeee eee eeeeeeeeeeeeee (eeeeeee MMMe8); eeeee: 888 ee (88%).

References


Cookie-Einstellungen