Ethyl Acetoacetate → 4-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acid

HRID 661488Notes

Reaction equation

HRID 661488 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[OH-].[Na+].[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=O.C([O-])([O-])=O.[Na+].[Na+]>P([O-])(O)(O)=O.[Na+].O>[CH2:21]([O:20][C:14]([C:15]1[C:4]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:3][NH:2][C:16]=1[CH3:18])=[O:19])[CH3:22]

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 713866726-Amino-5-oxohexanoic acid hydrochloride

Product 1

HCID 593760204-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 23672064Monosodium phosphateSolvent2×

Procedure

6-amino-5-oxohexanoic acid hydrochloride (S1) 22.44 g (0.12 mol) (Lartillot, Serge. et al, Bulletin de la Societe Chimique de France, 1964, 4:783) was solved in about 6.1 L sodium dihydrogen phosphate buffer (300 g sodium dihydrogen phosphate was solved in 6 L water, then Saturated sodium hydroxide aqueous solution was added until a pH of about 6.5 was reached), and ethyl acetoacetate 16.12 g (0.12 mol) was added to the above-mentioned solution. The reaction solution was refluxed for half an hour, cooled to room temperature and Na2CO3 was added until a pH of about 8 was reached. The mixture was extracted with 100 ml CHCl3 and Aqueous phase was acidified with 6 mol/L HCl to pH 1. The brown solid was collected by filtration, washed with water and dried in vacuum condition to give 20.29 g (71%) 4-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acid (S2).

Workup

  1. additionwas added to the above-mentioned solution
  2. temperatureThe reaction solution was refluxed for half an hour
  3. extractionThe mixture was extracted with 100 ml CHCl3 and Aqueous phase
  4. filtrationThe brown solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuum condition

Sources & evidence

ORD record
ord-ab1722fc6e934c0da08fe8402505c25d
Source dataset
uspto-grants-2011_12
Patent number
US08084621B2

Reaction notes

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