Potassium Carbonate → Phenyl 5-(2-methyl-1-morpholinopropan-2-yl)isoxazol-3-ylcarbamate

HRID 871677Notes

Reaction equation

HRID 871677 reaction equation
[CH3:1][C:2]([C:11]1[O:15][N:14]=[C:13]([NH2:16])[CH:12]=1)([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25]>C1COCC1>[CH3:10][C:2]([C:11]1[O:15][N:14]=[C:13]([NH:16][C:24](=[O:25])[O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=1)([CH3:1])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 668764135-(2-Methyl-1-morpholinopropan-2-yl)isoxazol-3-amine

Product 1

HCID 66876285Phenyl 5-(2-methyl-1-morpholinopropan-2-yl)isoxazol-3-ylcarbamateYield 637%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 5-(2-methyl-1-morpholinopropan-2-yl)isoxazol-3-amine (20 mg, 0.010 mmol) and potassium carbonate (25 mg, 0.181 mmol) in THF (6 mL) at 0° C., was added dropwise phenyl chloroformate (0.010 mL, 0.08 mmol). The reaction mixture was warmed to rt and stirred for a further 15 h. The reaction mixture was filtrated and the filtrate washed with saturated aqueous sodium carbonate, then brine, and concentrated under reduced pressure. The residue was dissolved in dichoromethane and dried over sodium sulfate then filtrated. The filtrate was concentrated under reduced pressure to give the crude product. Purification via recrystallization from a mixture of diethyl ether and hexanes, afforded phenyl 5-(2-methyl-1-morpholinopropan-2-yl)isoxazol-3-ylcarbamate (22 mg) which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. washthe filtrate washed with saturated aqueous sodium carbonate
  3. concentrationbrine, and concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichoromethane
  5. dry with materialdried over sodium sulfate
  6. filtrationthen filtrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give the crude product
  9. customPurification
  10. customvia recrystallization
  11. additionfrom a mixture of diethyl ether and hexanes

Sources & evidence

ORD record
ord-e0e1eaf26f94479bac749193c4311809
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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