Trifluoroacetic acid → HCID 15888101, compound

HRID 2395366Notes

Reaction equation

HRID 2395366 reaction equation
C(O[C:6]([N:8]([CH2:17][C:18]#[C:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[O:27][CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:30]=2)[CH:21]=1)[O:9]C(OC(C)(C)C)=O)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].C[Si]([N:53]=C=O)(C)C>ClCCl>[C:31]1([C@@H:29]2[CH2:28][O:27][C:26]([C:22]3[CH:21]=[C:20]([C:19]#[C:18][CH2:17][N:8]([OH:9])[C:6]([NH2:53])=[O:7])[CH:25]=[CH:24][CH:23]=3)=[N:30]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 70696Trimethylsilyl isocyanateHCID 516892Sodium BicarbonateHCID 18665573HCID 18665573, compound

Product 1

HCID 15888101HCID 15888101, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,O-di(tert-butoxycarbonyl)-[3-[3-(4,5-dihydro-4(R)-phenyl-oxazol-2-yl)phenyl]-2-propyn-1-yl]hydroxylamine (1.99 g, 4 mmol) in dichloromethane (30 ml) cooled to 0° C. was slowly added trifluoroacetic acid (10 ml). The reaction mixture was allowed to warm to room temperature, stirred an additional 30 min., and then poured into a saturated aqueous NaHCO3 solution (100 ml). The mixture was extracted with dichloromethane (3×30 ml) and the organic phase washed with brine (20 ml), dried (MgSO4) and evaporated. The resulting residue was dissolved in tetrahydrofuran (20 ml) and trimethylsilyl isocyanate (0.84 ml, 6.3 mmol) added. After stirring for 10 min. precipitation of product occurred. Methanol (1 ml) was added and solvent was removed by evaporation. The resulting solids were recrystallized from ethyl acetate to afford the title compound (0.98 g, 72 %) as white solids.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×30 ml)
  2. washthe organic phase washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe resulting residue was dissolved in tetrahydrofuran (20 ml)
  6. stirringAfter stirring for 10 min.
  7. customprecipitation of product
  8. additionMethanol (1 ml) was added
  9. customsolvent was removed by evaporation
  10. customThe resulting solids were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-dbd3d141277e4aa8ae0ea90a2f871235
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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