Potassium Carbonate → HCID 66794313, compound

HRID 1038322Notes

Reaction equation

HRID 1038322 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([CH2:12][OH:13])([CH2:10][OH:11])[CH2:8][OH:9])[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>C1COCC1>[OH:11][CH2:10][C:7]([C:5]1[O:4][N:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=1)([CH2:12][OH:13])[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 667939922-(3-Aminoisoxazol-5-yl)-2-(hydroxymethyl)propane-1,3-diol

Product 1

HCID 66794313HCID 66794313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2-(3-aminoisoxazol-5-yl)-2-(hydroxymethyl)propane-1,3-diol (1 equivalent) and potassium carbonate (2-5 equivalents) in anhydrous THF at rt is added phenyl chloroformate (1-2 equivalents), then 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 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-(hydroxymethyl)propan-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 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-b96fcb2ccd9e424d8e0f7e5997862a83
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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