Trifluoroacetic acid → HCID 58909401, compound

HRID 1985102Notes

Reaction equation

HRID 1985102 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=1)[C@H:9]([OH:25])[CH2:10][NH:11][C@@H:12]1[C:21]2[C:16](=[C:17]([Br:24])[CH:18]=[C:19]([CH2:22][CH3:23])[CH:20]=2)[CH2:15][CH2:14][CH2:13]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:26][C:27]1[CH:28]=[C:29]([F:34])[CH:30]=[C:31]([F:33])[CH:32]=1)[C@H:9]([OH:25])[CH2:10][NH:11][C@@H:12]1[C:21]2[C:16](=[C:17]([Br:24])[CH:18]=[C:19]([CH2:22][CH3:23])[CH:20]=2)[CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58909442HCID 58909442, compound

Product 1

HCID 58909401HCID 58909401, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3 (995 mg) is dissolved in 10 mL of anhydrous CH2Cl2 followed by the addition of 10 mL of trifluoroacetic acid (anhydrous). The solution stands for 90 min. then the volatiles are removed with a stream of nitrogen. The compound is desalted by extraction between ethyl acetate, 10 mL, and saturated aqueous sodium bicarbonate, 20 mL. The ethyl acetate phase is washed a second time with saturated sodium bicarbonate. The organic phase is then dried with MgSO4 (anhydrous), filtered, and evaporated of volatiles yielding 865 mg of 4 ([M+H]+=452.8).

Workup

  1. customthe volatiles are removed with a stream of nitrogen
  2. extractionThe compound is desalted by extraction between ethyl acetate, 10 mL, and saturated aqueous sodium bicarbonate, 20 mL
  3. washThe ethyl acetate phase is washed a second time with saturated sodium bicarbonate
  4. dry with materialThe organic phase is then dried with MgSO4 (anhydrous)
  5. filtrationfiltered
  6. customevaporated of volatiles

Sources & evidence

ORD record
ord-abbd91f589404d38b502bf3c4ac78be5
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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