8-Quinolineboronic acid → HCID 10115303, compound

HRID 459292Notes

Reaction equation

C([O:3][C:4](=[O:27])[C@@H:5]([O:25][CH3:26])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)C.[N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][C:36]=2B(O)O)[CH:31]=[CH:30][CH:29]=1>>[CH3:26][O:25][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:36]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:37]=3[N:28]=[CH:29][CH:30]=[CH:31]4)=[CH:22][CH:23]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:27]

Participants

Reactant 2

HCID 27343808-Quinolineboronic acid

HCID 58822720HCID 58822720, compound

Product 1

HCID 10115303HCID 10115303, compound

Procedure

The title compound was prepared from (2S)-3-{4-[3-(4-iodo-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester (Example 270, Step A) and 8-quinoline boronic acid by following the procedure described for Example 270 (Steps B and C). 1H-NMR (MeOD, 300.15 MHz): δ 8.82 (d, 1H, J=2.6), 8.39 (d, 1H, J=8.1), 7.92 (d, 1H, J=7.9), 7.74–7.63 (m, 2H), 7.58–7.51 (m, 3H), 7.18 (d, 2H, J=8.5), 7.08 (d, 2H, J=8.7), 6.88 (d, 2H, J=8.7), 4.28 (t, 2H, J=6.0), 4.20 (t, 2H, J=6.3), 3.90–3.80 (m, 1H), 3.30 (s, 3H), 3.04–2.84 (m, 2H), 2.29 (qn, 2H, J=6.3).

Sources & evidence

ORD record: ord-28c63f51ecbf421a92a835104d47e069
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Reaction notes

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