Trifluoroacetic acid → HCID 66953122, compound

HRID 2261060Notes

Reaction equation

HRID 2261060 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@H:12]1[C:24]([O:26][CH3:27])=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]1[C:24]([O:26][CH3:27])=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66953038HCID 66953038, compound

Product 1

HCID 66953122HCID 66953122, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 260C (1.01 g, 2.58 mmol) in dichloromethane (50 mL) at 0° C. was treated with TFA (5 mL). The reaction mixture was stirred at 0° C. for 1.0 hour then allowed to slowly warm to room temperature and stirred for an additional 2.0 hours. The mixture was concentrated, and then azeotropically evaporated with MeOH and toluene. The residue was dissolved in dichloromethane and washed with saturated NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give 0.61 g (yield: 81%) of Compound 260D as an oil. It was used in the next step without further purification.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringstirred for an additional 2.0 hours
  3. concentrationThe mixture was concentrated
  4. customazeotropically evaporated with MeOH and toluene
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with saturated NaHCO3 (2×50 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-328c19c175fb4f57928e8c38ccb9d77a
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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