(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

HRID 55299Notes

Reaction equation

HRID 55299 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=2)[N:7]=1.Br[CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1>>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]/[C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)=[CH:10][CH:9]=[C:8]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=2)[N:7]=1

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 677037393-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 677038293-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl esterYield 54.8%

Procedure

Under the conditions of example 1 D, 600 mg of 3-{3-hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester is reacted with 460 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene, worked up, and the crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate. 504 mg of 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate

Sources & evidence

ORD record
ord-c52d4b4eca1d46cab6977cba95a46e59
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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