2-Furanpropionic acid → HCID 68816692, compound

HRID 730025

Reaction equation

HRID 730025 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][C:8]([OH:10])=O.[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([CH:20]([NH2:22])[CH3:21])=[CH:12]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O.C(N(CC)CC)C>[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]([CH:20]([NH:22][C:8](=[O:10])[CH2:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH3:21])=[CH:12]1

Participants

8

Reactant 4

HCID 702862-Furanpropionic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14152978α-Methylbenzo[b]thiophene-3-methanamine

Product 1

HCID 68816692HCID 68816692, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

3-(2-Furyl)propionic acid (368 mg), 1-(benzothiophen-3-yl)ethylamine (443 mg), N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride (575 mg), 1-hydroxybenzotriazole (405 mg), and triethylamine (304 mg) were added to dehydrated dimethylformamide (DMF, 15 mL), and stirred at room temperature for 12 hours. The reaction mixture was added with water, and extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 628 mg of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8742676b326040279d416fe2de78f1dd
Source dataset
uspto-grants-2009_09
Patent number
US07582658B2

Linked notes

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