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

HRID 81870Notes

Reaction equation

HRID 81870 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.[CH3:49][O:50][C:51]([C:53]1[CH:58]=[CH:57][C:56](B(O)O)=[CH:55][CH:54]=1)=[O:52]>>[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:57]=[CH:58][C:53]([C:51]([O:50][CH3:49])=[O:52])=[CH:54][CH:55]=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 27343694-Methoxycarbonylphenylboronic acidHCID 66728422Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 68075900Methyl 4'-((N-(3-(Benzyloxy)-4-(Benzyloxycarbonyl)Phenyl)-2-(N,4-Dimethylphenyl-Sulfonamido)Acetamido)Methyl)Biphenyl-4-Carboxylate

Procedure

Aryl halide 9 was coupled to 4-(methoxycarbonyl)phenylboronic acid to give 31, on a 0.1 mmol scale via General Procedure H (53 mg, 52%): δH (400 MHz, CDCl3) 2.39 (s, 3H, CH3), 2.82 (s, 3H, CH3), 3.68 (s, 2H, CH2), 3.93 (s, 3H, CH3), 4.84 (s, 2H, CH2), 5.03 (s, 2H, CH2), 5.34 (s, 2H, CH2), 6.64 (s, 1H, CH), 6.68 (dd, J=8.4 and 1.2 Hz, 1H, CH), 7.19 (d, J=8.0 Hz, 2H, CH), 7.23-7.34 (m, 8H, CH), 7.37-7.40 (m, 2H, CH), 7.50-7.54 (m, 3H, CH), 7.60 (d, J=8.0 Hz, 2H, CH), 7.22 (d, J=8.4 Hz, 2H, CH), 7.70 (dd, J=5.6 and 3.2 Hz, 1H, CH), 7.83 (d, J=8.0 Hz, 1H, CH) 8.09 (d, 2H, J=8.4 Hz, CH); δC (100 MHz, CDCl3) 21.4, 36.0, 51.4, 52.1, 52.8, 67.0, 70.7, 114.1, 120.0, 120.9, 126.8, 126.9, 127.3, 127.4, 128.0, 128.2, 128.2, 128.5, 128.6, 128.7, 129.0, 129.4, 129.5, 130.1, 132.4, 133.1, 135.3, 135.7, 135.7, 136.5, 139.3, 143.3, 144.8, 144.9, 158.8, 166.8, 167.0, 167.7; LRMS (ES+) calcd for [C46H42N2O8S+H] 783.27 found 783.26.

Sources & evidence

ORD record
ord-6a9c8f24627a456e837aedb9e560871c
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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