4-Methoxycarbonylphenylboronic acid → methyl 4'-((N-(3-(benzyloxy)-4-(benzyloxycarbonyl)phenyl)-2-(N,4-dimethyl phenylsulfonamido)acetamido)methyl)terphenyl-4-carboxylate

HRID 81876Notes

Reaction equation

HRID 81876 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](C3C=CC(Br)=CC=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]C1C=CC=CC=1)=[O:12])C1C=CC=CC=1.[CH3:55][O:56][C:57]([C:59]1[CH:64]=[CH:63][C:62](B(O)O)=[CH:61][CH:60]=1)=[O:58]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[C:46]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:45]([C:62]3[CH:63]=[CH:64][C:59]([C:57]([O:56][CH3:55])=[O:58])=[CH:60][CH:61]=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:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:12])[C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:10]=1

Participants

3

Reactant 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 89765210benzyl 2-(Benzyloxy)-4-(N-((4'-bromo-[1,1'-biphenyl]-4-yl)methyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 131731898methyl 4'-((N-(3-(benzyloxy)-4-(benzyloxycarbonyl)phenyl)-2-(N,4-dimethyl phenylsulfonamido)acetamido)methyl)terphenyl-4-carboxylate

Procedure

Aryl halide 5 was coupled to 4-(methoxycarbonyl)phenylboronic acid to give 39 on a 0.1 mmol scale via General Procedure H (59 mg, 47%): δH (400 MHz, CDCl3) 2.38 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.69 (s, 2H, CH2), 3.93 (s, 3H, CH3), 4.84 (s, 2H, CH2), 5.02 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.64 (s, 1H, CH), 6.70 (dd, J=8.4 and 1.6 Hz, 1H, CH), 7.20 (d, J=8.0 Hz, 2H, CH), 7.24-7.28 (m, 6H, CH), 7.30-7.33 (m, 5H, CH), 7.36-7.41 (m, 3H, CH), 7.54 (d, J=8.4 Hz, 2H, CH), 7.61 (d, J=8.4 Hz, 2H, CH), 7.64-7.73 (m, 6H, CH), 7.85 (d, J=8.4 Hz, 1H, CH). LRMS (ES+) calcd for [C52H46N2O8S+H] 881.29. found 881.39.

Sources & evidence

ORD record
ord-ec92c5ed9a2d46f7b22677a97eb84ba3
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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