Potassium Carbonate → Methyl 2-((3 S,5S)-3,5-dimethylmorpholino)benzoxazole-4-carboxylate

HRID 249882Notes

Reaction equation

HRID 249882 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][C@H:16]1[CH2:21][O:20][CH2:19][C@H:18]([CH3:22])[NH:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:15][C@@H:16]1[N:17]([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:18]([CH3:22])[CH2:19][O:20][CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11768549(3S,5S)-3,5-DimethylmorpholineHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66873866Methyl 2-((3 S,5S)-3,5-dimethylmorpholino)benzoxazole-4-carboxylateYield 89.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (620 mg, 2.96 mmol) and (3S,5S)-3,5-dimethylmorpholine (341 mg, 2.96 mmol) and potassium carbonate (1.0 g, 7.4 mmol), in DMF (15 mL), was stirred in a 35° C. oil bath. After 17 h, the reaction mixture was cooled to ambient temperature, diluted with H2O (50 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with H2O (3×20 mL), brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure. Methyl 2-((3 S,5S)-3,5-dimethylmorpholino)benzoxazole-4-carboxylate (770 mg, 89%) was obtained as an amber oil. 1H NMR consistent.

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic layers were washed with H2O (3×20 mL), brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c7bd5b3b8374680b59be6377500de2b
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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