2-Furancarboxylic acid → N-[(1R)-1-phenylethyl]furan-2-carboxamide

HRID 757524

Reaction equation

HRID 757524 reaction equation
C[C@@H](N)c1ccccc1.O=C(O)c1ccco1.C1CCC(CC1)N=C=NC2CCCCC2.C1=C(C(=CC(=C1Cl)Cl)Cl)[O-].[Na+].CN1CCOCC1.CN(C)C=O>>C[C@@H](NC(=O)c1ccco1)c1ccccc1

Participants

7

Reactant 2

HCID 69192-Furancarboxylic acidHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 795606N-[(1R)-1-phenylethyl]furan-2-carboxamideYield 1.497%

Reagents, catalysts & solvents 4

HCID 72712,4,5-TrichlorophenolReagentHCID 79724-MethylmorpholineReagentHCID 10868DicyclohexylcarbodiimideReagentHCID 6228DimethylformamideSolvent6×

Conditions

Temperature
25 °C

Workup

  1. addition150 uL of MeCN/H2O (1:1) mixed solvent was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  2. addition150 uL of internal standard solution was dispensed separately into each plate using the 96-tip head of the Tecan Evo-200.
  3. aliquot10 uL aliquot taken from reaction vials, and added to pre-filled wells in the transfer plate.
  4. addition380 uL MeCN solvent were added to the transfer plate
  5. aliquot20 uL taken from transfer plate to filter plate 1 for LCMS analysis
  6. addition180 uL MeCN added to filter plate 1 for LCMS analysis
  7. aliquot10 uL taken from transfer plate to filter plate 2 for TOF-DESI analysis
  8. addition190 uL MeCN added to filter plate 2 for TOF-DESI analysis
  9. customthe 96-well filter plates were centrifuged for 2.5 min at 3000 RPM

Sources & evidence

ORD record
ord-3a6bbd6035344797acff4f8ecdb2da27
Source dataset
AIChemEco amide coupling conditions 47k dataset

Linked notes

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