Acetic Acid → HCID 11164862, compound

HRID 2261373Notes

Reaction equation

HRID 2261373 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[C:7](=[O:27])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:9][CH:10]=1.CO.[NH2:31][O:32][K].C(O)(=O)C>CO.C(Cl)(Cl)Cl>[OH:32][NH:31][C:3]([CH2:4][CH2:5][C:6]1[C:7](=[O:27])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:26])[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)[CH2:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 57443413HCID 57443413, compoundHCID 178514655HCID 178514655, compound

Product 1

HCID 11164862HCID 11164862, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

7 mg of compound (i) prepared by the above Step 2 was dissolved in methanol solution (0.02 mmol) and then 1.7 M methanolic suspension solution containing NH2OK (0.4 ml, 0.68 mmol) was added thereto at 0° C. and the resulting mixture was stirred for 8 hrs at room temperature. The resulting mixture was neutralized with 0.01 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 3.2 mg of N-{4-[3-(2-hydroxycarbamoyl-ethyl)-2-oxo-2,5-dihydro-pyrrole-1-yl-methyl]-phenyl}-benzamide (j) (yield: 46%).

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-b74c37d68e274b5189be225b63f2531f
Source dataset
uspto-grants-2010_12
Patent number
US07846963B2

Reaction notes

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