HCID 57413724, compound → HCID 57413591, compound

HRID 1428973Notes

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[C:57]([F:60])([F:59])[F:58])[C@H:35]1CC([O-])=O)(=O)C.[CH3:65][NH:66][C:67]([C:69]1[CH:70]=[C:71](B2OC(C)(C)C(C)(C)O2)[CH:72]=[C:73]([C:75]([NH:77][CH3:78])=[O:76])[CH:74]=1)=[O:68]>>[CH3:78][NH:77][C:75]([C:73]1[CH:72]=[C:71]([C:53]2[CH:54]=[CH:55][C:50]([O:49][C@@H:36]3[C@@H:35]([OH:16])[C@@H:34]([OH:33])[C@H:39]([OH:40])[C@@H:38]([CH2:44][OH:45])[O:37]3)=[C:51]([C:57]([F:58])([F:59])[F:60])[CH:52]=2)[CH:70]=[C:69]([C:67]([NH:66][CH3:65])=[O:68])[CH:74]=1)=[O:76]

Participants

Reactant 3

HCID 57413724HCID 57413724, compound

HCID 57413864HCID 57413864, compound

HCID 86674310HCID 86674310, compound

Product 1

HCID 57413591HCID 57413591, compoundYield 69%

Procedure

Using the procedure outlined in the synthesis of 5b with [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-trifluoromethyl-phenoxy)tetrahydropyran-3-yl]acetate (0.57 g) and N1,N3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxamide (9) (0.48 g), the title compound was obtained (0.340 g) in 69% yield for the two steps. 1H NMR (300 MHz, METHANOL-d4) δ ppm 8.17-8.24 (m, 1H), 8.14 (d, J=1.65 Hz, 2H), 7.92 (d, J=1.92 Hz, 1H), 7.87 (dd, J=2.20, 8.79 Hz, 1H), 7.57 (d, J=8.79 Hz, 1H), 5.64 (d, J=1.65 Hz, 1H), 4.04 (dd, J=1.65, 3.30 Hz, 1H), 3.87-3.96 (dd, 1H), 3.64-3.83 (m, 3H), 3.48-3.63 (m, 1H), 2.93 (s, 6H). MS (ESI): found: [M+H]+, 515.1.

Sources & evidence

ORD record: ord-bfbdb7dd8e384ce7a10d6a180b622a26
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937167B2

Reaction notes

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