Water → HCID 59272332, compound

HRID 1970288Notes

Reaction equation

HRID 1970288 reaction equation
[CH3:1][C:2](=[CH2:30])[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:16]2[O:15][C:14]3[C:9](=[CH:10][C:11]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)=[CH:12][CH:13]=3)[C@@:8]3([CH2:28][O:27][C:26]([NH2:29])=[N:25]3)[C:7]=2[CH:6]=1.O.S(=O)(=O)(O)[OH:33].C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:29][C:26]1[O:27][CH2:28][C@:8]2([N:25]=1)[C:9]1[CH:10]=[C:11]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:12]=[CH:13][C:14]=1[O:15][C:16]1[C:7]2=[CH:6][C:5]([O:4][CH2:3][C:2]([CH3:1])([OH:33])[CH3:30])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 59272329HCID 59272329, compound

Product 1

HCID 59272332HCID 59272332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A vial was charged with (S)-2′-(2-methylallyloxy)-7′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (41.17 mg, 0.103 mmol) and water (0.5 mL) giving a suspension. Sulfuric acid (110 μL, 2.061 mmol) was added, and the mixture became a cloudy solution. The vial was sealed and placed in a 70° C. oil bath for 8 h. The mixture was cooled to RT, and potassium carbonate was added until bubbling ceased. The resulting suspension was extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was chromatographed on a 12-g Redi-Sep column eluting with 0-10% MeOH/DCM to give a white solid. The solid was dissolved in methanol and purified further by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA). The fractions containing product were combined in saturated aq. sodium bicarbonate solution and extracted with DCM (3×). The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to give (S)-1-(2-amino-2′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yloxy)-2-methylpropan-2-ol as a white solid. MS m/z=418.2 [M+H]+. Calculated Mass for C24H24N3O4: 418.2.

Workup

  1. customgiving a suspension
  2. customThe vial was sealed
  3. customplaced in a 70° C.
  4. customfor 8 h
  5. customuntil bubbling
  6. extractionThe resulting suspension was extracted with DCM (3×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was chromatographed on a 12-g Redi-Sep column
  11. washeluting with 0-10% MeOH/DCM
  12. customto give a white solid
  13. custompurified further by reverse-phase HPLC (10-90% CH3CN/H2O with 0.1% TFA)
  14. additionThe fractions containing product
  15. extractionextracted with DCM (3×)
  16. dry with materialThe combined organic extracts were dried over sodium sulfate
  17. filtrationfiltered
  18. customevaporated

Sources & evidence

ORD record
ord-d229c12949144b66ab3393b6004bf9a3
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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