Hydrochloric Acid → 2-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 2191503Notes

Reaction equation

HRID 2191503 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:29])=[C:8](C(OC(C)(C)C)=O)[NH:9][C:10]=1[CH2:11][CH2:12][C:13](=[O:21])[NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[O:5])[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:29])=[CH:8][NH:9][C:10]=1[CH2:11][CH2:12][C:13](=[O:21])[NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592500615-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Product 1

HCID 592500792-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

5-[2-(2-Acetylamino-ethylcarbamoyl)-ethyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 62a (818 mg, 2 mmol) was dissolved in 5 ml of ethanol under stirring, and added with hydrochloric acid solution (5 ml, 12 mol/L) to the solution at room temperature. Upon completion of the addition, the reaction mixture was heated at 60° C. in an oil bath for 2 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was concentrated under reduced pressure to evaporate ethanol, adjusted to about pH 12 with aqueous sodium hydroxide solution (10%) and extracted with ethyl acetate (20 ml×3). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure to obtain the title compound 2-[2-(2-acetylamino-ethylcarbamoyl)-ethyl]-4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 62b (600 mg, yield 97%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto evaporate ethanol
  4. extractionextracted with ethyl acetate (20 ml×3)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1911aebd0f14bd58d481ece5d81c5f0
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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