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

HRID 1028169Notes

Reaction equation

HRID 1028169 reaction equation
OC([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][CH:21]1[CH2:26]COC[CH2:22]1)(C)C.Cl.[OH-].[Na+]>O1CCCC1>[CH3:26][C:21]1([CH3:22])[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 87745649Tert-butyl 5-(1-hydroxy-1-methylethyl)-4-[2-(tetrahydro-2h-pyran-4-yloxy)ethyl]-1,3-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 3D (4.6 g, 11 mmol) in tetrahydrofuran was added conc. HCl (6.9 mL). The reaction mixture was refluxed overnight and then cooled to room temperature. 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 using an Analogix® IT280™ (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 overnight
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4d271d94be87446092c4fc238530debb
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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