8-Bromo-2,6-dimethyloct-2-ene → 3-{6-[2-(4-methoxycarbonylphenyl)-ethinyl]-3-[(3RS)-3,7-dimethyl-6-octenyloxy]-2-pyridyl}-propionic acid methyl ester

HRID 55270

Reaction equation

HRID 55270 reaction equation
[CH3:1][O:2][C:3](=[O:25])[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]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=2)[N:7]=1.Br[CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34]>>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:27][CH2:28][CH:29]([CH3:36])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])=[CH:10][CH:9]=[C:8]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:20]=2)[N:7]=1

Participants

3

Reactant 2

HCID 43282458-Bromo-2,6-dimethyloct-2-eneHCID 541817313-{3-Hydroxy-6-[2-(4-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 541037463-{6-[2-(4-methoxycarbonylphenyl)-ethinyl]-3-[(3RS)-3,7-dimethyl-6-octenyloxy]-2-pyridyl}-propionic acid methyl esterYield 74.2%

Procedure

Under the conditions of example 1 D, 500 mg of 3-{3-hydroxy-6-[2-(4-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester is reacted with 354 mg of 1-bromo-(3RS)-3,7-dimethyl-6-octene, worked up, and the crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate. 522 mg of 3-{6-[2-(4-methoxycarbonylphenyl)-ethinyl]-3-[(3RS)-3,7-dimethyl-6-octenyloxy]-2-pyridyl}-propionic acid methyl ester is obtained as yellow oil.

Workup

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

Sources & evidence

ORD record
ord-2a7086b666994f6d93ad082df265dd08
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Linked notes

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