Acetic Acid → HCID 71460963, compound

HRID 2240589Notes

Reaction equation

HRID 2240589 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:9][CH:10]=1.[NH2:23][O:24][K].C(O)(=O)C>CO.CO.C(Cl)(Cl)Cl>[OH:24][NH:23][C:3](=[O:2])[CH2:4][CH2:5][C:6]1[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:9][CH:10]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 67453428HCID 67453428, compoundHCID 178514655HCID 178514655, compound

Product 1

HCID 71460963HCID 71460963, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

100 mg of 3-[2-oxo-1-(3-p-tolyl-propyl)-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (40ag) prepared by the above Step 7 was dissolved in methanol solution (0.33 mM) and then 1.7 M methanolic suspension solution containing NH2OK (0.82 ml, 5.0 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 50 mg of N-hydroxy-3-[2-oxo-1-(3-p-tolyl-propyl)-2,5-dihydro-1H-pyrrol-3-yl]-propionamide (40ah) (yield: 50%).

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-ae01b94e4f7747f8856f6bdf5e4f6ef5
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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