Acetic Acid → HCID 11276149, compound

HRID 2240609Notes

Reaction equation

HRID 2240609 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:15])[N:8]([CH2:12][CH:13]=[CH2:14])[CH2:9][CH2:10][CH:11]=1.[NH2:17][O:18][K].C(O)(=O)C>CO.C(OCC)(=O)C>[CH2:12]([N:8]1[CH2:9][CH2:10][CH:11]=[C:6]([CH2:5][CH2:4][C:3]([NH:17][OH:18])=[O:2])[C:7]1=[O:15])[CH:13]=[CH2:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167205483-(1-Allyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 11276149HCID 11276149, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

24 mg of 3-(1-allyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester (i1) prepared from the above Step 2 was dissolved in methanol solution (0.11 mM) and then 0.122 ml of 1.7M NH2OK suspension solution (0.207 mM) was added thereto at 0° c. and 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 solution, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:10) solvent mixture as an eluant to give 11 mg of the title compound (j1) (yield: 48%).

Workup

  1. customat 0°
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting compound was purified by column chromatography on Silica gel with methanol/chloroform (1:10) solvent mixture as an eluant

Sources & evidence

ORD record
ord-5cb32b194c12456da4e597e80b663639
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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