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

HRID 81873Notes

Reaction equation

HRID 81873 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:57]=[CH:56][C:55](B(O)O)=[CH:54][CH:53]=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:55]3[CH:56]=[CH:57][C:52]([C:49](=[O:51])[NH2:50])=[CH:53][CH:54]=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 27378114-Aminocarbonylphenylboronic acidHCID 66728422Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 68076518Benzyl 2-(Benzyloxy)-4-(N-((4'-Carbamoylbiphenyl-4-Yl)Methyl)-2-(N,4-Dimethyl Phenylsulfonamido)Acetamido)Benzoate

Procedure

Aryl halide 9 was coupled to 4-carbamoylphenylboronic acid to give 34 on a 0.1 mmol scale via General Procedure H (62 mg, 49%): δH (400 MHz, CDCl3) 2.38 (s, 3H, CH3), 2.82 (s, 3H, CH3), 3.68 (s, 2H, CH2), 4.39 (s, 2H, CH2), 5.03 (s, 2H, CH2), 5.34 (s, 2H, CH2), 5.91 (s, 1H, NH2), 6.44 (s, 1H, NH), 6.65 (s, 1H, CH2), 6.68 (d, 1H, CH), 7.19 (d, J=6.0 Hz, 2H, CH), 7.24-7.35 (m, 4H, CH), 7.38-7.41 (m, 2H, CH), 7.44-7.50 (m, 6H, CH), 7.53 (d, J=4.8 Hz, 1H, CH), 7.59 (s, 2H, CH), 7.61 (s, 2H, CH), 7.64 (d, J=5.4 Hz, 2H, CH), 7.68 (d, J=5.4 Hz, 2H, CH), 7.83 (d, J=6.3 Hz, 1H, CH), 7.89 (d, J=6.0 Hz, 2H, CH); δC (100 MHz, CDCl3) 21.3, 35.9, 51.3, 52.7, 66.9, 70.6, 113.9, 119.9, 120.8, 126.8, 126.9, 127.1, 127.3, 127.9, 128.1, 128.1, 128.3, 128.4, 128.4, 129.4, 131.8, 131.8, 131.8, 131.9, 132.0, 132.8, 133.0, 135.1, 135.5, 135.6, 136.3, 139.1, 143.2, 143.8, 144.8, 158.7, 165.2, 167.0, 168.8; LRMS (ES+) calcd for [C45H41N3O7S+H] 768.27 found 768.27.

Sources & evidence

ORD record
ord-143e2ccd80f046d3973801f3818fd430
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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