3-(Methoxycarbonyl)benzeneboronic acid → HCID 57413727, compound

HRID 1428969Notes

Reaction equation

CNC(=O)C1C=CC=C(C2C=CC([O:16][C@@H]3[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=C(C)C=2)C=1.C([O:33][C@@H:34]1[C@@H:39]([O:40]C(=O)C)[C@@H:38]([CH2:44][O:45]C(=O)C)[O:37][C@H:36]([O:49][C:50]2[CH:55]=[CH:54][C:53](Br)=[CH:52][C:51]=2[Cl:57])[C@H:35]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]>>[Cl:57][C:51]1[CH:52]=[C:53]([C:68]2[CH:67]=[C:66]([CH:71]=[CH:70][CH:69]=2)[C:64]([O:63][CH3:62])=[O:65])[CH:54]=[CH:55][C:50]=1[O:49][C@@H:36]1[C@@H:35]([OH:16])[C@@H:34]([OH:33])[C@H:39]([OH:40])[C@@H:38]([CH2:44][OH:45])[O:37]1

Participants

Reactant 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acid

HCID 57413864HCID 57413864, compound

HCID 86674308HCID 86674308, compound

Product 1

HCID 57413727HCID 57413727, compoundYield 43%

Procedure

4b was prepared using the same procedure as for 5b with [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-chloro-phenoxy)tetrahydropyran-3-yl]acetate and 3-methoxycarbonylphenyl boronic acid as the reactants. It was further purified by HPLC (C18, 15*150 mm column; eluent: acetonitrile/water (0.1% TFA)). Yield: 43%. 1H NMR (300 MHz, METHANOL-d4) δ ppm 3.59-3.71 (m, 1H) 3.71-3.85 (m, 3H) 3.94 (s, 3H) 4.01 (dd, J=9.34, 3.30 Hz, 1H) 4.12 (dd, J=3.30, 1.92 Hz, 1H) 5.61 (d, J=1.65 Hz, 1H) 7.40-7.49 (m, 1H) 7.49-7.62 (m, 2H) 7.68 (d, J=2.20 Hz, 1H) 7.82 (ddd, J=7.76, 1.85, 1.10 Hz, 1H) 7.98 (dt, J=7.83, 1.30 Hz, 1H) 8.14-8.25 (m, 1H). MS (ESI): found [M+H]+, 425.1.

Workup

customIt was further purified by HPLC (C18, 15*150 mm column; eluent: acetonitrile/water (0.1% TFA))

Sources & evidence

ORD record: ord-76b2aacb772842709510947525f2fc88
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937167B2

Reaction notes

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