Trifluoroacetic acid → 2-Amino-6,6-dimethylfuro[3,4-d]thiazol-4(6h)-one

HRID 78504Notes

Reaction equation

HRID 78504 reaction equation
[CH3:1][C:2]1([CH3:19])[C:9]2[S:8][C:7]([NH:10]C(=O)OC(C)(C)C)=[N:6][C:5]=2[C:4](=[O:18])[O:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:10][C:7]1[S:8][C:9]2[C:2]([CH3:1])([CH3:19])[O:3][C:4](=[O:18])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86618914Tert-butyl 6,6-dimethyl-4-oxo-4,6-dihydrofuro[3,4-d]thiazol-2-ylcarbamate

Product 1

HCID 875189862-Amino-6,6-dimethylfuro[3,4-d]thiazol-4(6h)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 249A (7.4 g, 26.0 mmol) in CH2Cl2 (20 mL) was added trifluoroacetic acid (20.0 mL, 260 mmol) slowly at 0° C. The reaction mixture was stirred at room temperature for 3 hours, and then concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL) and neutralized with saturated aqueous NaHCO3 solution. The layers were separated and the aqueous phase was extracted with ethyl acetate (5×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford the title compound. MS (ESI+) m/z 185 (M+H)+

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (5×100 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-894236621ac944e185b6475ce2bec794
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

Loading…