Water → HCID 117987968, compound

HRID 2206031Notes

Reaction equation

HRID 2206031 reaction equation
[NH2:1][CH:2]=[C:3]([C:8]1[N:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:10]=[CH:11][C:12]=1[C:13](OC)=[O:14])[C:4]([O:6][CH3:7])=[O:5].CC(C)([O-])C.[Na+].O>CN(C=O)C>[CH:17]1([N:9]2[C:8]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:2][NH:1][C:13](=[O:14])[C:12]=3[CH:11]=[CH:10]2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 131735824HCID 131735824, compound

Product 1

HCID 117987968HCID 117987968, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of methyl 2-(1-amino-3-methoxy-3-oxoprop-1-en-2-yl)-1-cyclopentyl-1H-pyrrole-3-carboxylate (20.45 g) in DMF (205 mL) was added sodium tert-butoxide (6.72 g), and the mixture was stirred at 160° C. for 1 hr. The reaction mixture was allowed to be cooled to room temperature, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with ethyl acetate and hexane to give the title compound (7.83 g).

Workup

  1. temperatureto be cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-8ad826a66a0b4abfb41cba0c4601adea
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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