Potassium Hydroxide → HCID 59654109, compound

HRID 2052791Notes

Reaction equation

HRID 2052791 reaction equation
[NH2:1][CH:2]([CH2:7][NH2:8])[C:3]([O:5][CH3:6])=[O:4].[OH-].[K+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=O)=O)=[CH:14][CH:13]=1>CO.C(Cl)Cl>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:8]=[CH:7][C:2]([C:3]([O:5][CH3:6])=[O:4])=[N:1][C:20]=2[C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 769961,2-Bis(4-methylphenyl)-1,2-ethanedioneHCID 428813HCID 428813, compound

Product 1

HCID 59654109HCID 59654109, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 2,3-diaminopropionate example 1A (2.4 g, 12.6 mmol) was shaken vigorously for 5 min in a solution of KOH (2.1 g, 37.7 mmol) in 20 mL of MeOH. The resulting milky solution was filtered to remove the solids, and the filtrate was added to a solution of 4,4′-dimethylbenzil (4.48 g, 18.8 mmol) in 20 mL of MeOH. The resulting mixture was heated to 65° C. for 14 h with a reflux condenser open to air. Solvent was evaporated and the residue was dissolved in 300 mL of EtOAc and 200 mL of 1N HCl. The layers were extracted and the organic layer was evaporated to give a thick oil that was redissolved in 5 mL of CH2Cl2 and this solution was loaded onto dry 120 g silica cartridge. The solvent was evaporated with a stream of N2, and the desired product example 1B was eluted with a gradient of 0-40% EtOAc/hexanes to give 1.71 g of a yellow solid.

Workup

  1. filtrationThe resulting milky solution was filtered
  2. customto remove the solids
  3. customSolvent was evaporated
  4. dissolutionthe residue was dissolved in 300 mL of EtOAc
  5. extractionThe layers were extracted
  6. customthe organic layer was evaporated
  7. customto give a thick oil that
  8. customonto dry 120 g silica cartridge
  9. customThe solvent was evaporated with a stream of N2
  10. washthe desired product example 1B was eluted with a gradient of 0-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-f9a53af822de4b89b4e30e39dbabfd38
Source dataset
uspto-grants-2008_02
Patent number
US07326706B2

Reaction notes

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