Acetic Acid → HCID 11412771, compound

HRID 2240592Notes

Reaction equation

HRID 2240592 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:12])[N:8]([CH3:11])[CH2:9][CH:10]=1.[NH2:14][O:15][K].C(O)(=O)C>CO.CO.C(Cl)(Cl)Cl>[OH:15][NH:14][C:3](=[O:2])[CH2:4][CH2:5][C:6]1[C:7](=[O:12])[N:8]([CH3:11])[CH2:9][CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57443425Methyl 3-(1-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)propanoateHCID 178514655HCID 178514655, compound

Product 1

HCID 11412771HCID 11412771, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

18 mg of 3-(1-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-propionic acid methyl ester (2g) prepared by the above Step 2 was dissolved in methanol solution (0.1 mM) and then 1.7 M methanolic suspension solution containing NH2OK (0.09 ml, 0.15 mM) was added thereto at 0° C. and the resulting mixture was stirred for 1 hr at room temperature. The resulting mixture was neutralized with 0.03 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 EtOAc and methanol (5:2) as an eluant to give 11 mg of N-hydroxy-3-(1-methyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-propionamide (2h) (yield: 59%).

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 EtOAc and methanol (5:2) as an eluant

Sources & evidence

ORD record
ord-c980c5224ce54fae8208962948fb12b7
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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