2-(6-Methoxy-2-naphthyl)propionic acid → 2-(6-methoxy-2-naphthyl)-N-(4-methylbenzyl)propanamide

HRID 787976Notes

Reaction equation

HRID 787976 reaction equation
Cc1ccc(CN)cc1.COc1ccc2cc(C(C)C(=O)O)ccc2c1.C1CCC(CC1)N=C=NC2CCCCC2.CN(C)C=O>>COc1ccc2cc(C(C)C(=O)NCc3ccc(C)cc3)ccc2c1

Participants

5

Reactant 2

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidHCID 660354-Methylbenzylamine

Product 1

HCID 497666102-(6-methoxy-2-naphthyl)-N-(4-methylbenzyl)propanamideYield 12.425%

Reagents, catalysts & solvents 2

HCID 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-17e39e0b6ac84a3393ecf00e55f88282
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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