3-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester → 3-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethyl]-2-pyridyl}-propionic acid-methyl ester

HRID 55300Notes

Reaction equation

HRID 55300 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>CO.[Pd]>[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]([CH2:13][CH2:14][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

4

Reactant 1

HCID 677037393-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 537837203-{3-Hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethyl]-2-pyridyl}-propionic acid-methyl esterYield 52.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under the conditions of example 14 A, a solution of 500 mg of 3-{3-hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethinyl]-2-pyridyl}-propionic acid-methyl ester in 5 ml of methanol is hydrogenated in the presence of 50 mg of 10% palladium catalyston activated carbon and worked up. The crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate. 266 mg of 3-{3-hydroxy-6-[2-(4-methoxycarbonylmethylphenyl)-ethyl]-2-pyridyl}-propionic acid-methyl ester of melting point 90°-91° is obtained.

Workup

  1. customThe crude product is chromatographed on silica gel with hexane/0-30% ethyl acetate

Sources & evidence

ORD record
ord-1b530ebb08e4421a9e6d9fc4a06a0b49
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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