Potassium Carbonate → HCID 66874375, compound

HRID 249912Notes

Reaction equation

HRID 249912 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[CH3:15][N:16]1[CH2:21][C@H:20]([CH3:22])[NH:19][C@@H:18]([CH3:23])[C:17]1=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:23][C@H:18]1[C:17](=[O:24])[N:16]([CH3:15])[CH2:21][C@H:20]([CH3:22])[N:19]1[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylateHCID 66874385HCID 66874385, compound

Product 1

HCID 66874375HCID 66874375, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (342 mg, 1.62 mmol), (3S,5S)-1,3,5-trimethylpiperazin-2-one (230 mg, 1.62 mmol) and potassium carbonate (670 mg, 4.85 mmol), in DMF (10 mL), was stirred at ambient temperature for 16 h. The reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (2×40 mL). The combined organic layers were washed with 0.5 N HCl (10 mL), H2O (10 mL), brine (10 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solids were removed by filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 10% CH2Cl2 in EtOAc to 100% EtOAc) to give methyl 2-((2S,6S)-2,4,6-trimethyl-3-oxopiperazine-1-yl)benzoxazole-4-carboxylate (98 mg, 19%): 1H NMR consistent.

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. washThe combined organic layers were washed with 0.5 N HCl (10 mL), H2O (10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. customthe solids were removed by filtration
  8. concentrationThe filtrate was concentrated
  9. custompurified by column chromatography (silica gel, 10% CH2Cl2 in EtOAc to 100% EtOAc)

Sources & evidence

ORD record
ord-32c064fb881545ec84b2cea4fc16a2cb
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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