Trifluoroacetic acid → HCID 54076691, compound

HRID 2364877Notes

Reaction equation

HRID 2364877 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([O:16][CH3:17])([CH3:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+].ClC(OC)=O>C(Cl)Cl.CCOC(C)=O>[CH3:17][O:16][C:13]([CH3:15])([CH3:14])[C@H:9]([NH:8][C:6]([O:5][CH3:1])=[O:7])[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 59611493HCID 59611493, compound

Product 1

HCID 54076691HCID 54076691, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 203B (163 mg, 0.66 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (2 mL) and the solution was stirred at room temperature for 1 h. Solvent was removed in vacuo and the residue was suspended in saturated NaHCO3, extracted with EtOAc, the organic extracts combined, washed with brine, dried (Na2SO4), filtered and solvent removed in vacuo. The residue was dissolved in dioxane (1 mL) and 1 M NaOH (1.1 mL, 2.175 mmol) was added followed by the dropwise addition of methyl chloroformate (0.102 mL, 1.3 mmol). The solution was stirred at room temperature for 16 h, diluted with EtOAc, washed with 1 N HCl, brine, dried (Na2SO4), filtered and solvent removed in vacuo to give the title compound (96 mg, 0.468 mmol, 71%).

Workup

  1. customSolvent was removed in vacuo
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customsolvent removed in vacuo
  7. dissolutionThe residue was dissolved in dioxane (1 mL)
  8. stirringThe solution was stirred at room temperature for 16 h
  9. washwashed with 1 N HCl, brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-d2d92d53028e463b955c6cba89cf25be
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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