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

HRID 1028171Notes

Reaction equation

HRID 1028171 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>ClCCl>[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)-oneYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 5A (7.4 g, 26.0 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (20.0 ml, 260 mmol) slowly at 0° C. The reaction mixture was removed from the ice bath, allowed to reach room temperature and stirred for 3 hours. The reaction mixture was concentrated to dryness, diluted with ethyl acetate (100 mL) and neutralized with saturated NaHCO3 solution. The layers were separated and the aqueous layer was extracted with ethyl acetate (5×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to give 4.8 g (99%) of product as a white solid. MS (ESI+) m/z 185 (M+H)+.

Workup

  1. customThe reaction mixture was removed from the ice bath
  2. customto reach room temperature
  3. concentrationThe reaction mixture was concentrated to dryness
  4. additiondiluted with ethyl acetate (100 mL)
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (5×100 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8bc88f3676a84eb8a20a60aff0dff2e9
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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