Acetic Acid → HCID 11162137, compound

HRID 2240583Notes

Reaction equation

HRID 2240583 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:20])[N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[CH2:9][CH:10]=1.[NH2:22][O:23][K].C(O)(=O)C>CO.CO.C(Cl)(Cl)Cl>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][N:8]1[CH2:9][CH:10]=[C:6]([CH2:5][CH2:4][C:3]([NH:22][OH:23])=[O:2])[C:7]1=[O:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 57443418HCID 57443418, compoundHCID 178514655HCID 178514655, compound

Product 1

HCID 11162137HCID 11162137, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

38 mg of 3-{1-[2-(2-fluoro-phenyl)-ethyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-propionic acid methyl ester (x) prepared by the above Step 4 was dissolved in methanol solution (0.13 mM) and then 1.7 M methanolic suspension solution containing NH2OK (0.38 ml, 0.65 mM) was added thereto at 0° C. and the resulting mixture was stirred for 8 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 25 mg of 3-{1-[2-(2-fluoro-phenyl)-ethyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-N-hydroxy-propionamide (28y) (yield: 65%).

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-25de813544d841989cbdddb8cf454e23
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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