Butanoic acid, 4-chloro-4-oxo-, methyl ester → HCID 54215536, compound

HRID 248447Notes

Reaction equation

HRID 248447 reaction equation
[NH2:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[NH:5][C:4]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.C(N(C(C)C)CC)(C)C.[C:27]([CH2:31][CH2:32][C:33](Cl)=[O:34])([O:29][CH3:30])=[O:28]>C(Cl)Cl>[C:27]([CH2:31][CH2:32][C:33]([NH:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[NH:5][C:4]=1[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)=[O:34])([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 81531DiisopropylethylamineHCID 54273607HCID 54273607, compound

Product 1

HCID 54215536HCID 54215536, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 400 mg (1.54 mmol) of 3-aminomethyl-2,5-dithienylpyrrole (XVIII) and 378 ul (3.07 mmol) of diisopropylethylamine in 15 ml of anhydrous methylene chloride was added 3-carbomethoxypropionyl chloride (1.6 ml, 9.23 mmol). After stirring for 5 minutes at room temperature, the reaction mixture was quenched by the addition of 1 ml of water. The aqueous layer was extracted three times with 5 ml portions of chloroform and the combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude reaction product was chromatographed on 100 g of silica gel. Elution with chloroform:methanol, 95:5, gave 456 mg (39%) of the amide (XXVI) as a greenish solid having a mp of 48°-49° C., and Rf :0.55 (chloroform:methanol, 98:2).

Workup

  1. customthe reaction mixture was quenched by the addition of 1 ml of water
  2. extractionThe aqueous layer was extracted three times with 5 ml portions of chloroform
  3. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude reaction product
  7. customwas chromatographed on 100 g of silica gel
  8. washElution with chloroform

Sources & evidence

ORD record
ord-3a5a3a8e6aa24fc0b7bbc6185e224bc3
Source dataset
uspto-grants-1993_05
Patent number
US05210217

Reaction notes

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