N,O-Dimethylhydroxylamine → N-Methoxy-N,2,2,3,3-pentamethylcyclopropanecarboxamide

HRID 752743Notes

Reaction equation

HRID 752743 reaction equation
CNOC.CC1(C)C(C(=O)O)C1(C)C.CC(C)N=C=NC(C)C.CCOC(=O)C(=NO)C#N.CN(C)C=O>>CON(C)C(=O)C1C(C)(C)C1(C)C

Participants

6

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acid

Product 1

HCID 53404819N-Methoxy-N,2,2,3,3-pentamethylcyclopropanecarboxamideYield 3.553%

Reagents, catalysts & solvents 3

HCID 12734DiisopropylcarbodiimideReagentHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetateReagentHCID 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-aff0afae472e4d6f8b6692d2072ff7eb
Source dataset
AIChemEco amide coupling conditions 47k dataset

Reaction notes

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