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

HRID 2240611Notes

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.[NH2:15][O:16][K].C(O)(=O)C>CO.C(OCC)(=O)C>[OH:16][NH:15][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 mM) and then 0.122 ml of 1.7M NH2OK suspension solution in methanol (0.207 mM) 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 of the title compound (j2) (yield: 35%).

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-5077e34e76a2477fa6fdb510c5f28b8e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723376B2

Reaction notes

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