Hydrochloric Acid → HCID 23144704, compound

HRID 337423Notes

Reaction equation

HRID 337423 reaction equation
[NH2:1][C:2]1[S:3][C:4]([N:12]2[CH2:21][CH2:20][C:15]3(OCC[O:16]3)[CH2:14][CH2:13]2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[NH2:1][C:2]1[S:3][C:4]([N:12]2[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]2)=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23144162HCID 23144162, compound

Product 1

HCID 23144704HCID 23144704, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-4-(2-furyl)thiazole (1.00 g, 3.25 mmol) obtained in Step 1 was dissolved in THF (10 mL), 2 mol/L hydrochloric acid (5 mL) was added thereto, followed by stirring under heating and reflux for 4 hours. The reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1) to afford 2-amino-4-(2-furyl)-5-(4-oxopiperidino)thiazole (151 mg, 18%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 4 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-2dbd3eba79144fa092554fff55ca6230
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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