Valeryl chloride → HCID 5215686, compound

HRID 1276143Notes

Reaction equation

HRID 1276143 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16][CH3:17])=[O:15]>N1C=CC=CC=1>[C:1]([NH:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 5215686HCID 5215686, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

3.8 ml of n-pentanoic acid chloride was added to 50 ml of an anhydrous pyridine solution containing 5.0 g of methyl 3-aminothiophene-2-carboxylate at 0° C. The mixture was stirred at 0° C. for 1 hour and further stirred at room temperature for 2 hours. The reaction mixture was concentrated, diluted with ethyl acetate and washed with 1N chloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in this order. Ethyl acetate was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (elution with n-hexane:ethyl acetate=5:1) to provide 7.0 g of methyl 3-pentanoylaminothiophene-2-carboxylate as a colorless oily compound.

Workup

  1. stirringfurther stirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with 1N chloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in this order
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution with n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ca95cb1c8e6d472a9c43260dc8dc2065
Source dataset
uspto-grants-2000_12
Patent number
US06166016

Reaction notes

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