Acetic Acid → 1,2,5,6-Tetrahydro-N-hydroxy-1-methyl-2-oxo-3-pyridinepropanamide

HRID 2261407Notes

Reaction equation

C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:13])[N:8]([CH3:12])[CH2:9][CH2:10][CH:11]=1.CO.[NH2:17][O:18][K].C(O)(=O)C>C(OCC)(=O)C>[OH:18][NH:17][C:3](=[O:2])[CH2:4][CH2:5][C:6]1[C:7](=[O:13])[N:8]([CH3:12])[CH2:9][CH2:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

50 mg of 3-(1-methyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester prepared from the above Step 1 was dissolved in methanol (0.25 mmol) and then 0.12 ml of 1.7M NH2OK suspension solution in methanol (0.21 mmol) was added thereto at 0° C. and the resulting mixture was stirred for 3 hrs at room temperature. The resulting mixture was neutralized with 0.02 ml of acetic acid, diluted with 10 ml of ethyl acetate, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant to give 19 mg (yield: 35%) of the title compound (j2).

Workup

filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:20) solvent mixture as an eluant

Sources & evidence

ORD record: ord-4c2cc5b17a38433099080b57bf09b5f5
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846963B2

Reaction notes

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