Triethylamine → HCID 54139884, compound

HRID 1276382Notes

Reaction equation

HRID 1276382 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH2:22]([O:24][C:25]1[C:26](=O)[C:27](=[O:32])[C:28]=1[O:29]CC)[CH3:23]>C(O)C>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH:6][C:26]1[C:27](=[O:32])[C:28](=[O:29])[C:25]=1[O:24][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 123228Diethyl squarate

Product 1

HCID 54139884HCID 54139884, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of L-phenylalanine methyl ester HCl (2.0 mmol, 431 mg) in absolute ethanol (20 mL) was added triethylamine (2.2 mmol, 202 mg; 278 μL) and the resulting solution was stirred at room temperature for 15 minutes. Subsequently, neat 3,4-diethoxy-3-cyclobutene-1,2-dione (2 mmol, 340 mg; 296 μL) was added dropwise and 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) and purified by flash chromatography (SiO2 :1) 20% EtOAc/hexane; 2) 30% EtOAc/hexane; 3) 40% EtOAc/hexane) to afford the title compound as a colorless oil (551 mg; 85%).

Workup

  1. stirringthe resulting solution was stirred at room temperature overnight, during which a white solid
  2. customprecipitated out of solution
  3. customThe volatiles were removed in vacuo
  4. custompartitioned between EtOAc and water
  5. dry with materialThe organics were dried (Na2SO4)
  6. custompurified by flash chromatography (SiO2 :1) 20% EtOAc/hexane

Sources & evidence

ORD record
ord-c30f0d0f3124466ca0f1081a738fa5f0
Source dataset
uspto-grants-2000_12
Patent number
US06166050

Reaction notes

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