Hydrochloric Acid → HCID 59541833, compound

HRID 2388349Notes

Reaction equation

HRID 2388349 reaction equation
C[O:2][C:3]1[S:4][C:5]([C:8]2(O)[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:6][N:7]=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[O:12]=[C:11]1[CH2:16][CH2:17][C:8]([C:5]2[S:4][C:3](=[O:2])[NH:7][CH:6]=2)=[CH:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59541813HCID 59541813, compound

Product 1

HCID 59541833HCID 59541833, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-(2-Methoxy-thiazol-5-yl)-1,4-dioxa-spiro[4.5]decan-8-ol (as prepared in the previous step, 1.05 g, 3.87 mmol) was treated with 6N HCl (˜2 mL) in THF (5 mL) at room temperature for 4 hours. The reaction was neutralized with saturated NaHCO3 solution and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow solid, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as white solid.

Workup

  1. customthe solvent was removed
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow solid, which
  8. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-dbb19d1c05674a4094011bcc74a24266
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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