Réaction #169058

ord-ec92c5ed9a2d46f7b22677a97eb84ba3

Équation de réaction

Cc1ccc(S(=O)(=O)N(C)CC(=O)N(Cc2ccc(-c3ccc(Br)cc3)cc2)c2ccc(C(=O)OCc3ccccc3)c(OCc3ccccc3)c2)cc1
Aryl halide
Cc1ccc(S(=O)(=O)N(C)CC(=O)N(Cc2ccc(-c3ccc(Br)cc3)cc2)c2ccc(C(=O)OCc3ccccc3)c(OCc3ccccc3)c2)cc1
benzyl 2-(benzyloxy)-4-(N((4′-bromo-[1,1′-biphenyl]-4-yl)methyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate
COC(=O)c1ccc(B(O)O)cc1
4-(methoxycarbonyl)phenylboronic acid
COC(=O)c1ccc(-c2ccc(CN(C(=O)CN(C)S(=O)(=O)c3ccc(C)cc3)c3ccc(C(=O)OCc4ccccc4)c(OCc4ccccc4)c3)cc2-c2ccccc2)cc1
39
COC(=O)c1ccc(-c2ccc(CN(C(=O)CN(C)S(=O)(=O)c3ccc(C)cc3)c3ccc(C(=O)OCc4ccccc4)c(OCc4ccccc4)c3)cc2-c2ccccc2)cc1
methyl 4′-((N-(3-(benzyloxy)-4-(benzyloxycarbonyl)phenyl)-2-(N,4-dimethyl phenylsulfonamido)acetamido)methyl)terphenyl-4-carboxylate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Aryl halide 5 was coupled to 4-(methoxycarbonyl)phenylboronic acid to give 39 on a 0.1 mmol scale via General Procedure H (59 mg, 47%): δH (400 MHz, CDCl3) 2.38 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.69 (s, 2H, CH2), 3.93 (s, 3H, CH3), 4.84 (s, 2H, CH2), 5.02 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.64 (s, 1H, CH), 6.70 (dd, J=8.4 and 1.6 Hz, 1H, CH), 7.20 (d, J=8.0 Hz, 2H, CH), 7.24-7.28 (m, 6H, CH), 7.30-7.33 (m, 5H, CH), 7.36-7.41 (m, 3H, CH), 7.54 (d, J=8.4 Hz, 2H, CH), 7.61 (d, J=8.4 Hz, 2H, CH), 7.64-7.73 (m, 6H, CH), 7.85 (d, J=8.4 Hz, 1H, CH). LRMS (ES+) calcd for [C52H46N2O8S+H] 881.29. found 881.39.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08846707B2uspto-grants-2014_09