Tetrabutylammonium Fluoride → (S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879264Notes

Reaction equation

HRID 879264 reaction equation
[Br:1][C:2]1[S:3][C:4]2[C:10]([O:11]S(C(F)(F)F)(=O)=O)=[C:9]([C@H:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=2[N:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[S:3][C:4]2[C:10]([OH:11])=[C:9]([C@H:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:30])=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86699785(S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 71003373(S)-ethyl 2-(2-bromo-7-hydroxy-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate (32): (500 mg, 0.938 mmol) in THF (5 mL) was added TBAF (1.0 M in THF, 4 mL) slowly. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was washed by a mixture of H2O (20 mL) and HOAc (200 ul), extracted by EtOAc, the organic phase was washed by sat. NaHCO3, dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-40% EtOAc in hexanes to give 75A (380 mg). LCMS-ESI+: calc'd for C16H20BrNO4S: 402.0 (M+H+); Found: 401.9 (M+H+).

Workup

  1. washThe reaction mixture was washed by a mixture of H2O (20 mL) and HOAc (200 ul)
  2. extractionextracted by EtOAc
  3. washthe organic phase was washed by sat. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. custompurified by silica gel column
  8. washeluting by 0-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-ca05d1f11c854cdb9cef37fc7e47cd5b
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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