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

HRID 81867Notes

Reaction equation

HRID 81867 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41]C2C=CC(Br)=CC=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])C1C=CC=CC=1.[CH3:49][O:50][C:51]([C:53]1[CH:54]=[C:55](B(O)O)[CH:56]=[CH:57][CH:58]=1)=[O:52]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:15]2[CH:20]=[CH:19][C:18]([C:55]3[CH:56]=[CH:57][CH:58]=[C:53]([C:51]([O:50][CH3:49])=[O:52])[CH:54]=3)=[CH:17][CH:16]=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:30])=[O:31])[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:9]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:10]=1

Participants

3

Reactant 2

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 66728422Benzyl 2-(benzyloxy)-4-(N-(4-bromobenzyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 68075984Methyl 4'-((N-(3-(Benzyloxy)-4-(Benzyloxycarbonyl)Phenyl)-2-(N,4-Dimethylphenyl-Sulfonamido)Acetamido)Methyl)Biphenyl-3-Carboxylate

Procedure

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.

Sources & evidence

ORD record
ord-47a8ad7872e2474bb7d2ed748e871fe0
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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