Benzylamine → HCID 15479332, compound

HRID 1276383Notes

Reaction equation

HRID 1276383 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@H:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5][C:6]1[C:9](=O)[C:8](=[O:11])[C:7]=1[O:12]CC.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[CH3:1][O:2][C:3](=[O:22])[C@H:4]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH:5][C:6]1[C:7](=[O:12])[C:8](=[O:11])[C:9]=1[NH:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 54139884HCID 54139884, compound

Product 1

HCID 15479332HCID 15479332, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of [2-ethoxy-3,4-dioxo-cyclobut-1-enyl]-L-phenylalanine methyl ester (0.33 mmol, 100 mg) in absolute ethanol (3 mL) was added neat benzylamine (0.36 mmol, 39 mg; 40 μL) dropwise at room temperature. The resulting solution was stirred at room temperature overnight, during which a white solid precipitated out of solution. The volatiles were removed in vacuo and the residue was taken up in EtOAc and partitioned between EtOAc and water. The organics were dried (Na2SO4), concentrated in vacuo and purified by flash chromatography (SiO2 :EtOAc/hexane) to afford the title compound as a white solid (113 mg; 94%).

Workup

  1. customprecipitated out of solution
  2. customThe volatiles were removed in vacuo
  3. custompartitioned between EtOAc and water
  4. dry with materialThe organics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2 :EtOAc/hexane)

Sources & evidence

ORD record
ord-daf7287692d342019e86af419c734119
Source dataset
uspto-grants-2000_12
Patent number
US06166050

Reaction notes

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