Potassium Iodide → 3-Hydroxy-3-(3-methoxy-2-oxo-1,2-dihydro-pyridin-4-yl)-pentanoic acid tert-butyl ester

HRID 2246192Notes

Reaction equation

[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]([C:12]1[CH:17]=[CH:16][N:15]=[C:14]([O:18]C)[C:13]=1[O:20][CH3:21])([OH:11])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[I-].[K+]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:22])[CH2:7][C:8]([OH:11])([C:12]1[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=1[O:20][CH3:21])[CH2:9][CH3:10])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

The mixture of 3-(2,3-dimethoxy-pyridin-4-yl)-3-hydroxy-pentanoic acid tert-butyl ester (6) (3.6 g; 11.56 mmol) and potassium iodide (8 g) in acetic acid (10 mL) was stirred at 60° C. for 16 hours. Reaction was checked by TLC and was not completed. The mixture was then heated at 73° C. for 2 days. The acetic acid was removed by evaporation under reduced pressure and dichloromethane (50 mL) was added. The solution was then washed with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatograph over silica gel (10 to 50% ethyl acetate/hexanes) provided 1.9 g of the ester, 3-hydroxy-3-(3-methoxy-2-oxo-1,2-dihydro-pyridin-4-yl)-pentanoic acid tert-butyl ester (7), as a white solid.

Workup

customReaction
temperatureThe mixture was then heated at 73° C. for 2 days
customThe acetic acid was removed by evaporation under reduced pressure and dichloromethane (50 mL)
additionwas added
washThe solution was then washed with saturated sodium bicarbonate solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by column chromatograph over silica gel (10 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-5009eba10bd14832836f58f81b715bab
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687487B2

Reaction notes

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