Diethyl Ether → HCID 57672924, compound

HRID 73842Notes

Reaction equation

HRID 73842 reaction equation
[OH-].[Na+].CO[C:5]([C:7]1([NH:13][C:14](=[O:22])[CH2:15][CH2:16][C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].CCOCC.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(Cl)Cl>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][CH2:15][C:14]1[O:22][C:5](=[O:6])[C:7]2([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[N:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 32472118Methyl 1-(3-(furan-2-yl)propanamido)cyclohexane-1-carboxylate

Product 1

HCID 57672924HCID 57672924, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.7 ml of 2N aqueous NaOH solution was added to a solution of 478 mg (1.7 mmol) of 1-[[1-oxo-3-(2-furanyl)propyl]amino]cyclohexanecarboxylic acid methyl ester obtained in Reference Example 64 in 2 ml of tetrahydrofuran, and the mixture was heated under reflux for 3 hours. Ether was added to the reaction solution to wash it. After the separated aqueous layer was neutralized by concentrated hydrochloric acid, it was extracted with ethyl acetate. After the obtained organic layer was washed with saturated brine, it was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Then, 10 ml of methylene chloride and 377 mg (1.82 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were added to the residue, and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, ethyl acetate was added thereto, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 198 mg (47%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washto wash it
  4. extractionwas extracted with ethyl acetate
  5. washAfter the obtained organic layer was washed with saturated brine, it
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  9. additionwas added
  10. washthe mixture was washed with water
  11. dry with materialby drying with anhydrous sodium sulfate
  12. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5475c4f07f6a424daacda4cc42dc9c63
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

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