Potassium Carbonate → HCID 66873354, compound

HRID 249894Notes

Reaction equation

HRID 249894 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.[CH2:15]([N:22]1[CH2:27][C@H:26]([CH3:28])[NH:25][C@@H:24]([CH3:29])[C:23]1=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:15]([N:22]1[CH2:27][C@H:26]([CH3:28])[N:25]([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)[C@@H:24]([CH3:29])[C:23]1=[O:30])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12197172HCID 12197172, compoundHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66873354HCID 66873354, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (970 mg, 4.58 mmol) and (3S,5S)-1-benzyl-3,5-dimethylpiperazin-2-one (1.00 g, 4.58 mmol) in DMF (20 mL), was stirred in a 35° C. oil bath. After 16 h, the reaction mixture was heated to 55° C. After 3 h, potassium carbonate (630 mg, 4.58 mmol) was added. The reaction mixture was stirred for 2 h at 55° C. and then at ambient temperature for 17 h. The reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with 0.5 N HCl (25 mL), H2O (25 mL), brine (25 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification by chromatography (silica gel, 10 to 80% EtOAc in hexanes) gave methyl 2-((2S,6S)-4-benzyl-2,6-dimethyl-3-oxopiperazine-1-yl)benzoxazole-4-carboxylate (1.08 g, 60%). 1H NMR consistent.

Workup

  1. temperaturethe reaction mixture was heated to 55° C
  2. waitAfter 3 h
  3. stirringThe reaction mixture was stirred for 2 h at 55° C.
  4. waitat ambient temperature for 17 h
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe combined organic layers were washed with 0.5 N HCl (25 mL), H2O (25 mL), brine (25 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customPurification by chromatography (silica gel, 10 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbc49de61db340d68c21479643df5e82
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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