3-Thiophenacetic acid → HCID 67574269, compound

HRID 1600538Notes

Reaction equation

HRID 1600538 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]([OH:9])=O)=[CH:2]1.Cl.CN(C)CCCN=C=NCC.[O:22]=[C:23]([CH3:33])[CH2:24][NH:25][C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:28]>ClCCl>[O:22]=[C:23]([CH3:33])[CH2:24][N:25]([C:7](=[O:9])[CH2:6][C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[C:26]([CH3:32])([CH3:31])[C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 234043-Thiophenacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21829906HCID 21829906, compound

Product 1

HCID 67574269HCID 67574269, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of thiophen-3-acetic acid (8.7 g) in dichloromethane (70 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (11.7 g), and the mixture was stirred for 10 minutes at room temperature. To the solution was added dropwise a solution of methyl 2-(2-oxopropylamino)isobutyrate (10.6 g) in dichloromethane (10 mL) at room temperature, and the mixture was then stirred for 24 hours at room temperature. After distilling off the solvent, water was added, and then the mixture was extracted with ethyl acetate. The extract was washed with a saturated sodium hydrogencarbonate aqueous solution and dried over anhydrous sodium sulfate. After distilling off ethyl acetate, 7.61 g of methyl 2-[N-(2-oxopropyl)thiophene-3-yl-acetylamino]isobutyrate was obtained.

Workup

  1. stirringthe mixture was then stirred for 24 hours at room temperature
  2. distillationAfter distilling off the solvent, water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium hydrogencarbonate aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off ethyl acetate

Sources & evidence

ORD record
ord-778972f8c736492ea8ad7f6e0e837bad
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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