Acetic Acid → 3-Pyrrolidineacetamide, N-hydroxy-2-oxo-1-(phenylmethyl)-

HRID 2261378Notes

Reaction equation

HRID 2261378 reaction equation
CO[C:3](=[O:19])[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14]C=2)[C:6]1=[O:18].CO.[NH2:22][O:23][K].C(O)(=O)C>CO.C(Cl)(Cl)Cl>[CH2:10]([N:7]1[CH2:8][CH2:9][CH:5]([CH2:4][C:3]([NH:22][OH:23])=[O:19])[C:6]1=[O:18])[C:11]1[CH:12]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 21750807Methyl [2-oxo-1-(2-phenylethyl)pyrrolidin-3-yl]acetateHCID 178514655HCID 178514655, compound

Product 1

HCID 112651463-Pyrrolidineacetamide, N-hydroxy-2-oxo-1-(phenylmethyl)-Yield 14%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

12 mg of (2-oxo-1-phenethyl-pyrrolidin-3-yl)-acetic acid methyl ester (25r) prepared by the above Step 1 was dissolved in methanol solution (0.04 mmol) and then 1.7 M methanolic suspension solution containing NH2OK (0.07 ml, 0.12 mmol) was added thereto at 0° C. and the resulting mixture was stirred for 4 hrs at room temperature. The resulting mixture was neutralized with 0.02 ml of acetic acid, diluted with 10% methanol/chloroform solution, filtered and concentrated in vacuo. The resulting compound was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1:9) as an eluant to give 1.6 mg of 2-(1-benzyl-2-oxo-pyrrolidin-3-yl)-N-hydroxy-acetamide (25s) (yield: 8%).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe resulting compound was purified by Silica gel column chromatography with a solvent mixture
  5. additionmixed with methanol and chloroform (1:9) as an eluant

Sources & evidence

ORD record
ord-86ec883440e04f789e7bc776cd791364
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

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