Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate → (2S)-4'-{3-[2-Methoxy-4-(2-methoxy-2-methoxycarbonyl-ethyl)-phenoxy]-propoxy}-biphenyl-4-carboxylic acid methyl ester

HRID 459277Notes

Reaction equation

HRID 459277 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([O:19][CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15]Br)=[C:8]([O:17][CH3:18])[CH:7]=1.[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25]>>[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:15][CH2:14][CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6]([CH2:5][C@H:4]([O:19][CH3:20])[C:3]([O:2][CH3:1])=[O:21])=[CH:7][C:8]=3[O:17][CH3:18])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25]

Participants

3

Reactant 2

HCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylateHCID 694249483-[4-(3-Bromo-propoxy)-3-methoxy-phenyl]-2-methoxy-propionic acid methyl ester

Product 1

HCID 58822569(2S)-4'-{3-[2-Methoxy-4-(2-methoxy-2-methoxycarbonyl-ethyl)-phenoxy]-propoxy}-biphenyl-4-carboxylic acid methyl ester

Procedure

3-[4-(3-Bromo-propoxy)-3-methoxy-phenyl]-2-methoxy-propionic acid methyl ester (Step A) and 4′-hydroxy-biphenyl-4-carboxylic acid methyl ester (Example 197, Step A) were treated under Mitsunobu standard condition B. The crude was purified by chromatography on silica gel (hexanes/ethyl acetate 7:3) to afford the title compound.

Workup

  1. customThe crude was purified by chromatography on silica gel (hexanes/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-ec93558ec036430ea7be2ddbe8b01dd7
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

Loading…