Pyridine → HCID 2767879, compound

HRID 131278Notes

Reaction equation

HRID 131278 reaction equation
[NH2:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH:17]1([C:20]([NH:1][C:2]2[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[O:21])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 5072225Methyl 5-aminofuran-2-carboxylate

Product 1

HCID 2767879HCID 2767879, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-aminofuran-2-carboxylate (1.0 g) and pyridine (1.2 mL) in methylene chloride (6.0 mL) is added dropwise cyclopropanecarbonyl chloride (0.78 mL) under ice-cooling and the mixture is stirred at room temperature for 2 hours. To the reaction mixture is added a saturated sodium hydrogencarbonate solution and the mixture is extracted with chloroform. The extract is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=3:1) to give methyl 5-[(cyclopropylcarbonyl)amino]furan-2-carboxylate (0.82 g, yield; 56%) as colorless crystals. MS (APCI) m/z: 210 [M+H]+

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. dry with materialThe extract is dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a5b746bcf22c4bbebb1f69f502c5fde3
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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