3-(Methoxycarbonyl)benzeneboronic acid → HCID 57413728, compound

HRID 1428970Notes

Reaction equation

HRID 1428970 reaction equation
CNC(=O)C1C=CC=C([C:10]2[CH:15]=[CH:14][C:13]([O:16][C@@H:17]3[C@@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]3)=[C:12]([CH3:28])[CH:11]=2)C=1.C(O[C@@H]1[C@@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H](OC2C=CC(Br)=CC=2C)[C@H]1CC([O-])=O)(=O)C.[CH3:62][O:63][C:64]([C:66]1[CH:67]=[C:68](B(O)O)[CH:69]=[CH:70][CH:71]=1)=[O:65]>>[CH3:28][C:12]1[CH:11]=[C:10]([C:68]2[CH:67]=[C:66]([CH:71]=[CH:70][CH:69]=2)[C:64]([O:63][CH3:62])=[O:65])[CH:15]=[CH:14][C:13]=1[O:16][C@@H:17]1[C@@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]1

Participants

4

Reactant 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 57413864HCID 57413864, compoundHCID 86674309HCID 86674309, compound

Product 1

HCID 57413728HCID 57413728, compoundYield 54%

Procedure

4c was prepared using the same procedure as for 5b with [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl]acetate and 3-methoxycarbonylphenyl boronic acid as the reactants. Yield: 54%. 1H NMR (300 MHz, METHANOL-d4) δ ppm 8.20 (t, J=1.51 Hz, 1H), 7.94 (td, J=1.41, 7.90 Hz, 1H), 7.77-7.87 (m, 1H), 7.52 (t, J=7.55 Hz, 1H), 7.39-7.48 (m, 2H), 7.27-7.38 (m, 1H), 5.56 (d, J=1.65 Hz, 1H), 4.08 (dd, J=1.92, 3.30 Hz, 1H), 3.94-4.01 (m, 1H), 3.90-3.94 (m, 3H), 3.68-3.83 (m, 3H), 3.55-3.65 (m, 1H), 2.31 (s, 3H). MS (ESI): found [M+Na]+, 427.1

Sources & evidence

ORD record
ord-81471e4599a64762a6b999e0b2db0d1c
Source dataset
uspto-grants-2015_01
Patent number
US08937167B2

Reaction notes

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