Réaction #2254196

ord-49cac3d09a504c3dbe96f9ebd63c1781

Équation de réaction

Cc1c(C)c(S(=O)(=O)NC(=N)NCCC[C@H](N)C(=O)O)c(C)c2c1OC(C)(C)C2
(S)-2-Amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl) guanidino)pentanoic acid
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)N[C@@H](CCCNC(=N)NS(=O)(=O)c1c(C)c(C)c2c(c1C)CC(C)(C)O2)C(=O)O
(S)-2-acetamido-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl) guanidino)pentanoic acid

Réactifs

Cc1c(C)c(S(=O)(=O)NC(=N)NCCC[C@H](N)C(=O)O)c(C)c2c1OC(C)(C)C2
(S)-2-Amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl) guanidino)pentanoic acid
CC(=O)OC(C)=O
acetic anhydride
—
primary amine

Réactifs

Aucun

Solvants

c1ccncc1
pyridine

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreafter 1 h the reaction is quenched with aqueous acid
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    Autrepurified by chromatography

Mode opératoire

(S)-2-Amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl) guanidino)pentanoic acid (H-L-Arg(Pbf)-OH) (1.0 eq.) is dissolved in pyridine (0.25 M) and acetic anhydride (1.2 eq.) is added to acylate the primary amine, after 1 h the reaction is quenched with aqueous acid, extracted with ethyl acetate, and purified by chromatography to afford (S)-2-acetamido-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl) guanidino)pentanoic acid (Ac-L-Arg(Pbf)-OH).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09044464B2uspto-grants-2015_06