3-Pyridinylboronic acid → (2S)-2-Methoxy-3-{4-[3-(4-pyridin-3-yl-phenoxy)-propoxy]-phenyl}-propionic acid

HRID 459290Notes

Reaction equation

HRID 459290 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[CH:33]=[CH:32][CH:31]=[C:30](B(O)O)[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:30]3[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=3)=[CH:22][CH:23]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:27]

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 58822720(2S)-3-{4-[3-(4-iodo-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester

Product 1

HCID 58822855(2S)-2-Methoxy-3-{4-[3-(4-pyridin-3-yl-phenoxy)-propoxy]-phenyl}-propionic acid

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 3-pyridyl boronic acid by following the procedure described for Example 270 (Steps B and C). 1H-NMR (MeOD, 300.15 MHz): δ 8.76 (s, 1H), 8.46 (s, 1H), 8.05 (d, 1H, J=8.1), 7.60 (d, 2H, J=8.7), 7.49 (dd, 1H, J=7.7, 4.8), 7.19 (d, 2H, J=8.5), 7.09 (d, 2H, J=8.7), 6.85 (d, 2H, J=8.5), 4.24 (t, 2H, J=6.1), 4.17 (t, 2H, J=6.3), 3.74 (dd, 1H, J=8.7, 3.8), 3.27 (s, 3H), 2.97 (dd, 1H, J=14.3, 3.8), 2.81 (dd, 1H, J=14.1, 8.5), 2.26 (qn, 2H, J=6.0).

Sources & evidence

ORD record
ord-9d7616a886f54bbeb4ac5bd44f230d38
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…