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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 81869Generated: October 25, 2026

(3-Carbamoylphenyl)boronic acid → Benzyl 2-(Benzyloxy)-4-(N-((3'-Carbamoylbiphenyl-4-Yl)Methyl)-2-(N,4-Dimethyl Phenylsulfonamido)Acetamido)Benzoate

https://huagongshe.com/reaction/81869

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(3-Carbamoylphenyl)boronic acidHCID 2737814—
ReactantBenzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoateHCID 66728422—
ProductBenzyl 2-(Benzyloxy)-4-(N-((3'-Carbamoylbiphenyl-4-Yl)Methyl)-2-(N,4-Dimethyl Phenylsulfonamido)Acetamido)BenzoateHCID 68076487—

Reaction Steps

Aryl halide 9 was coupled to 3-carbamoylphenylboronic acid to give 30 on a 0.1 mmol scale via General Procedure H (57 mg, 52%): δH (400 MHz, CDCl3) 2.38 (s, 3H, CH3), 2.81 (s, 3H, CH3), 3.68 (s, 2H, CH2), 4.83 (s, 2H, CH2), 5.02 (s, 2H, CH2), 5.34 (s, 2H, CH2), 5.93 (s, 1H, NH2), 6.33 (s, 2H, NH2), 6.64 (s, 1H, CH), 6.67 (dd, J=6.0 and 1.2 Hz, 1H, CH), 7.18 (d, J=6.0 Hz, 2H, CH), 7.31-7.39 (m, 13H, CH), 7.50 (d, J=6.0 Hz, 2H, CH), 7.60 (d, J=6.3 Hz, 2H, CH), 7.70 (d, J=5.7 Hz, 1H, CH), 7.77 (d, J=5.7 Hz, 1H, CH), 7.83 (d, J=6.0 Hz, 1H, CH), 8.03 (s, 1H, CH); δC (100 MHz, CDCl3) 21.3, 35.9, 51.3, 52.7, 66.9, 70.6, 113.9, 119.2, 119.9, 126.0, 126.9, 127.0, 127.2, 127.3, 127.9, 128.1, 128.1, 128.4, 128.4, 128.7, 128.9, 129.2, 129.4, 130.3, 132.3, 133.0, 133.8, 135.1, 135.5, 135.6, 136.0, 139.4, 140.8, 143.3, 144.8, 158.7, 165.2, 167.0, 169.1; LRMS (ES+) calcd for [C45H41N3O7S+H]768.27 found 768.27.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846707B2
Source datasetuspto-grants-2014_09
ORD IDord-578a7f3b9a92432bb0ea4bf41722d3e4
Source noteuspto-grants-2014_09