Methanol → HCID 57443413, compound

HRID 2240574Notes

Reaction equation

HRID 2240574 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[C:7](=[O:19])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:9][CH:10]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(NC(C)C)(C)C.CO>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][C:6]1[C:7](=[O:19])[N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][CH:17]=2)[CH2:9][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 59305559HCID 59305559, compound

Product 1

HCID 57443413HCID 57443413, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

10 mg of 3-[1-(4-amino-benzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (h) prepared by above Step 1 was dissolved in methylene chloride solution (0.04 mM) at room temperature. And then 8.5 μl of benzoyl chloride (0.07 mM) and 19.1 μl of diisopropylamine (0.11 mM) were added thereto and the mixture was stirred for 2 hrs at 0° C. The reaction was stopped by adding methanol and the mixture was extracted three times with 10 ml of ethyl acetate. The organic layer was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified with Silica gel column chromatography with a solvent mixture mixed with ethyl acetate and hexane (1:2) as an eluant to give 12 mg of 3-[1-(4-benzoylamino-benzyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-propionic acid methyl ester (i) (yield: 87%).

Workup

  1. extractionthe mixture was extracted three times with 10 ml of ethyl acetate
  2. washThe organic layer was washed with saturated NaCl solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting compound was purified with Silica gel column chromatography with a solvent mixture
  7. additionmixed with ethyl acetate and hexane (1:2) as an eluant

Sources & evidence

ORD record
ord-1357c339c36c486bb41ef4b191ef6675
Source dataset
uspto-grants-2010_05
Patent number
US07723376B2

Reaction notes

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