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

HRID 81869Notes

Reaction equation

HRID 81869 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[CH:46][C:45](Br)=[CH:44][CH:43]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:49]([C:52]1[CH:53]=[C:54](B(O)O)[CH:55]=[CH:56][CH:57]=1)(=[O:51])[NH2:50]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([C:56]3[CH:55]=[CH:54][CH:53]=[C:52]([C:49](=[O:51])[NH2:50])[CH:57]=3)=[CH:44][CH:43]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2737814(3-Carbamoylphenyl)boronic acidHCID 66728422Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 68076487Benzyl 2-(Benzyloxy)-4-(N-((3'-Carbamoylbiphenyl-4-Yl)Methyl)-2-(N,4-Dimethyl Phenylsulfonamido)Acetamido)Benzoate

Procedure

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.

Sources & evidence

ORD record
ord-578a7f3b9a92432bb0ea4bf41722d3e4
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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