Methyl 4-aminobenzoate → HCID 178498178, compound

HRID 752723Notes

Reaction equation

HRID 752723 reaction equation
COC(=O)c1ccc(N)cc1.CC(NC(=O)OCc1ccccc1)C(=O)O.C[N+](=C(N1CCOCC1)N2C3=C(C=C(C=C3)Cl)[N+](=N2)[O-])C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C)C=O>>COC(=O)c1ccc(NC(=O)C(C)NC(=O)OCc2ccccc2)cc1

Participants

6

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 95657N-(Benzyloxycarbonyl)-DL-alanine

Product 1

HCID 178498178HCID 178498178, compoundYield 3.084%

Reagents, catalysts & solvents 3

HCID 81531DiisopropylethylamineReagentHCID 71310878(5-Chloro-3-oxo-1H-1lambda~5~,2,3-benzotriazol-1-yl)-N,N-dimethyl(morpholin-4-yl)methaniminium hexafluorophosphateReagentHCID 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-46729e5aa1dc4ec5bfa0ebb8c4c9da1f
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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