Ethyl chloroformate → 5-Carbamoylfuran-2-carboxylic Acid Benzyl Ester

HRID 34099Notes

Reaction equation

HRID 34099 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([C:16]([OH:18])=O)=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OCC)=O.O.[NH3:26].[Cl-].[NH4+]>O1CCCC1.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([C:11]1[O:12][C:13]([C:16](=[O:18])[NH2:26])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 12896473Azane;hydrateHCID 16091220Furan-2,5-dicarboxylic Acid Monobenzyl Ester

Product 1

HCID 600347845-Carbamoylfuran-2-carboxylic Acid Benzyl Ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

170 mg of furan-2,5-dicarboxylic acid monobenzyl ester was dissolved in 5 mL of tetrahydrofuran, and added with 144 μl of triethylamine. After cooling to 0° C., 72.3 μl of ethyl chloroformate was added dropwise and stirred at this temperature for 30 minutes. 1 mL of concentrated ammonia water was added and stirred at room temperature for 10 minutes, and then aqueous ammonium chloride was added to stop the reaction. After extracting the aqueous phase with ethyl acetate, the organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 185 mg of the title compound as white crystals.

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. customthe reaction
  3. extractionAfter extracting the aqueous phase with ethyl acetate
  4. washthe organic phase was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-06e895fce5144a5ca92846444e67f562
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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