Hydrochloric Acid → 4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine

HRID 538811Notes

Reaction equation

HRID 538811 reaction equation
O[C:2]([C:5]1[S:9][C:8]([NH:10]C(=O)OC(C)(C)C)=[N:7][C:6]=1[CH2:18][CH2:19][O:20]C1CCCCO1)([CH3:4])[CH3:3].Cl.[OH-].[Na+]>C1COCC1>[CH3:4][C:2]1([CH3:3])[C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH2:18][CH2:19][O:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 87179654Tert-butyl 5-(2-hydroxypropan-2-yl)-4-(2-(tetrahydro-2h-pyran-2-yloxy)ethyl)thiazol-2-ylcarbamate

Product 1

HCID 871793724,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amineYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 89D (4.6 g, 11 mmol) in THF (90 mL) was added conc. HCl (6.9 mL). The reaction mixture was refluxed for overnight and then cooled. The mixture was basified with 5N NaOH ((17 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-10% methanol in dichloromethane) to afford 1.04 g (51%) of the title compound. MS (ESI+) m/z 185 (M+H)+

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (SiO2, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3fe21f5bdde649dca86a714f8f3e263f
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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