Potassium Carbonate → HCID 66794001, compound

HRID 1038317Notes

Reaction equation

HRID 1038317 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH3:12])([CH2:10][OH:11])[CH2:8][OH:9])[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C1COCC1>[OH:9][CH2:8][C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)([CH3:12])[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 667940772-(3-Aminoisoxazol-5-yl)-2-methylpropane-1,3-diol

Product 1

HCID 66794001HCID 66794001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-(3-aminoisoxazol-5-yl)-2-methylpropane-1,3-diol (1 equivalent) and potassium carbonate (2-5 equivalents) in anhydrous THF at rt is added dropwise phenyl chloroformate (1-2 equivalents) and stirring is continued at rt until the reaction is substantially complete as monitored by LCMS or TLC. The mixture is concentrated under reduced pressure and the residue is partitioned between water and dichloromethane. The organic layer is separated and the aqueous layer is further extracted with dichloromethane. The combined organic extracts are washed with water or brine, then dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford phenyl 5-(1,3-dihydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate.

Workup

  1. customis continued at rt until the reaction
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is partitioned between water and dichloromethane
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is further extracted with dichloromethane
  6. washThe combined organic extracts are washed with water or brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-4d4186fe5ce24c71b48039a4e99d1b77
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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