3-(Methoxycarbonyl)benzeneboronic acid → methyl 4'-((N-(3-(benzyloxy)-4-(benzyloxycarbonyl)phenyl)-2-(N,4-dimethylphenyl sulfonamido)acetamido)methyl)terphenyl-3-carboxylate

HRID 81874Notes

Reaction equation

HRID 81874 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](C2C=CC(C)=CC=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:55][O:56][C:57]([C:59]1[CH:60]=[C:61](B(O)O)[CH:62]=[CH:63][CH:64]=1)=[O:58]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:43]=[C:44]([C:47]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:45]([C:63]3[CH:62]=[CH:61][CH:60]=[C:59]([C:57]([O:56][CH3:55])=[O:58])[CH:64]=3)=[CH:46][CH:47]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:11][C:10]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:9]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 89765210benzyl 2-(Benzyloxy)-4-(N-((4'-bromo-[1,1'-biphenyl]-4-yl)methyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 131731897methyl 4'-((N-(3-(benzyloxy)-4-(benzyloxycarbonyl)phenyl)-2-(N,4-dimethylphenyl sulfonamido)acetamido)methyl)terphenyl-3-carboxylateYield 38%

Procedure

Aryl halide 5 was coupled to 3-(methoxycarbonyl)phenylboronic acid on a 0.1 mmol scale via General Procedure H to yield 35 (39 mg, 38%): δH (400 MHz, CDCl3) 2.40 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.68 (s, 2H, CH2), 3.96 (s, 3H, CH3), 4.84 (s, 2H, CH2), 5.02 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.62 (s, 1H, CH), 6.70 (d, J=8.0 Hz, 1H, CH) 7.19 (d, J=8.0 Hz, 2H, CH), 7.26-7.34 (m, 10H, CH), 7.38-7.41 (m, 3H, CH), 7.54 (d, J=8.0 Hz, 2H, CH), 7.62 (d, J=8.4 Hz, 2H, CH), 7.68 (q, J=8.0 Hz, 4H, CH), 7.84 (t, J=8.0 Hz, 2H, CH), 8.03 (d, J=8.0 Hz, 1H, CH), 8.32 (s, 1H, CH); LRMS (ES+) Calcd for [C52H46N2O8S+H] 859.31. found 859.25.

Sources & evidence

ORD record
ord-833d2fc73e744095bba4443b2bf977cf
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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