1-(p-Hydroxyphenyl)imidazole → (2S)-3-{4-[3-(4-Imidazol-1-yl-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

HRID 459295Notes

Reaction equation

HRID 459295 reaction equation
C([O:3][C:4](=[O:20])[CH:5]([O:18][CH3:19])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16]Br)=[CH:9][CH:8]=1)C.[N:21]1([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:25]=[CH:24][N:23]=[CH:22]1>>[N:21]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:16][CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:18][CH3:19])[C:4]([OH:3])=[O:20])=[CH:12][CH:11]=3)=[CH:28][CH:27]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

3

Reactant 2

HCID 823151-(p-Hydroxyphenyl)imidazoleHCID 694251353-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 58822946(2S)-3-{4-[3-(4-Imidazol-1-yl-phenoxy)-propoxy]-phenyl}-2-methoxy-propionic acid

Procedure

3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester (Example 173, Step A) and 4-(imidazol-1-yl)phenol were treated under ester J to give the title compound. 1H-NMR (CDCl3, 200.15 MHz): δ 8.11 (s, 1H), 7.31–7.16 (m, 7H), 6.99 (d, 2H, J=8.9), 6.82 (d, 2H, J=8.6), 4.19 (t, 2H, J=6.2), 4.12 (t, 2H, J=5.9), 3.95 (dd, 1H, J=7.3, 4.8), 3.39 (s, 3H), 3.08 (dd, 1H, J=14.4, 4.8), 2.96 (dd, 1H, J=14.2, 7.6), 2.26 (qn, 2H, J=5.9).

Sources & evidence

ORD record
ord-2cdfa8a9aa024a408cf05a2d0dd5af39
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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