Reaction #83568

ord-6f9c6fc48ccb43daa6f56931b13dd79f

Reaction equation

$COC(=O)CCc1nc(/C=C\c2cccc(C(=O)OC)c2)ccc1OCCCC/C=C/c1ccc(OC)cc1$

3-{6-[2-(3-methoxycarbonyl-phenyl)-(1Z)-1-ethenyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

sodium hydroxide

→

$COc1ccc(/C=C/CCCCOc2ccc(/C=C\c3cccc(C(=O)O)c3)nc2CCC(=O)O)cc1$

title compound

Yield 88.9%

$COc1ccc(/C=C/CCCCOc2ccc(/C=C\c3cccc(C(=O)O)c3)nc2CCC(=O)O)cc1$

3-{6-[2-(3-Carboxyphenyl)-(1Z)-1-ethenyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid

Yield 88.9%

Reactants

$COC(=O)CCc1nc(/C=C\c2cccc(C(=O)OC)c2)ccc1OCCCC/C=C/c1ccc(OC)cc1$

3-{6-[2-(3-methoxycarbonyl-phenyl)-(1Z)-1-ethenyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

—

sodium hydroxide

Reagents

None

Solvents

methanol

tetrahydrofuran

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Procedure

Under the conditions of example 3 C, 82 mg of 3-{6-[2-(3-methoxycarbonyl-phenyl)-(1Z)-1-ethenyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester in 2.5 ml of methanol and 1 ml of tetrahydrofuran is saponified with 2 ml of 2n sodium hydroxide solution and worked up. 69 mg of the title compound is obtained as colorless oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05624943uspto-grants-1997_04