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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81867Generated: October 25, 2026

3-(Methoxycarbonyl)benzeneboronic acid → Methyl 4'-((N-(3-(Benzyloxy)-4-(Benzyloxycarbonyl)Phenyl)-2-(N,4-Dimethylphenyl-Sulfonamido)Acetamido)Methyl)Biphenyl-3-Carboxylate

https://huagongshe.com/reaction/81867

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-(Methoxycarbonyl)benzeneboronic acidHCID 2734714—
ReactantBenzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateHCID 66728422—
ProductMethyl 4'-((N-(3-(Benzyloxy)-4-(Benzyloxycarbonyl)Phenyl)-2-(N,4-Dimethylphenyl-Sulfonamido)Acetamido)Methyl)Biphenyl-3-CarboxylateHCID 68075984—

Reaction Steps

Aryl halide 9 was coupled to 3-(methoxycarbonyl)phenylboronic acid to give 28 on a 0.1 mmol scale via General Procedure H (65 mg, 62%): δH (400 MHz, CDCl3) 2.40 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.68 (s, 2H, CH2), 3.94 (s, 3H, CH3), 4.84 (s, 2H, CH2), 5.03 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.62 (s, 1H, CH), 6.68 (dd, J=8.0 and 1.6 Hz, 1H, CH), 7.19 (d, J=8.0 Hz, 2H, CH), 7.30-7.42 (m, 10H, CH), 7.52 (d, J=8.4 Hz, 2H, CH), 7.60-7.64 (m, 4H, CH), 7.78 (d, J=7.6 Hz, 2H, CH), 7.84 (d, 1H, J=8.0 Hz, CH), 8.02 (dt, J=8.0 and 1.2 Hz, 1H, CH), 8.25 (t, J=2.0 Hz, 1H, CH); δC (100 MHz, CDCl3) 21.5, 36.0, 52.2, 52.8, 56.0, 67.5, 70.7, 117.2, 117.5, 120.1, 125.2, 127.0, 127.2, 127.4, 127.5, 128.0, 128.1, 128.1, 128.2, 128.2, 128.5, 128.6, 128.9, 129.5, 130.7, 131.3, 133.2, 135.7, 135.7, 136.1, 139.5, 141.2, 142.4, 158.8, 161.7, 166.9, 167.0, 168.4; LRMS (ES+) calcd for [C46H42N2O8S+H] 783.27. found 783.26.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846707B2
Source datasetuspto-grants-2014_09
ORD IDord-47a8ad7872e2474bb7d2ed748e871fe0
Source noteuspto-grants-2014_09