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

HRID 459291Notes

Reaction equation

HRID 459291 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][C:31](B(O)O)=[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:31]3[CH:32]=[CH:33][N:28]=[CH:29][CH:30]=3)=[CH:22][CH:23]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:27]

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 58822720(2S)-3-{4-[3-(4-iodo-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid ethyl ester

Product 1

HCID 10294823(2S)-2-Methoxy-3-{4-[3-(4-pyridin-4-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 4-pyridyl boronic acid by following the procedure described for Example 270 (Steps B and C). 1H-NMR (CDCl3, 200.15 MHz): δ 8.67–8.65 (m, 2H), 8.16 (d, 2H, J=6.6), 7.90 (d, 2H, J=8.8), 7.16–7.09 (m, 4H), 6.82 (d, 2H, J=8.8), 4.26 (t, 2H, J=6.2), 4.13 (t, 2H, J=6.2), 3.90 (dd, 1H, J=7.7, 4.8), 2.97 (dd, 1H, J=14.3, 5.1), 2.83 (dd, 1H, J=14.3, 7.7), 2.24 (qn, 2H, J=5.9).

Sources & evidence

ORD record
ord-f74f40d54c3646b0a07a65ca51962cfa
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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