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

HRID 78507Notes

Reaction equation

HRID 78507 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+]>O1CCCC1>[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-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 251D (4.6 g, 11 mmol) in tetrahydrofuran was added concentrated HCl (6.9 mL). The reaction mixture was heated at reflux 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 CH2Cl2) to afford the title compound. MS (ESI+) m/z 185 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for overnight
  3. temperaturecooled
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2, 0-10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-ca7ffc71083a48c6acdf0aa048c6f2e4
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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