Trifluoroacetic acid → HCID 67247178, compound

HRID 2425323Notes

Reaction equation

HRID 2425323 reaction equation
FC(F)(F)C(O)=O.C([O:12][P:13](=[O:52])([O:47]C(C)(C)C)[O:14][CH2:15][C:16]([NH:43]C(=O)C)([CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:32]=2)[CH2:27]1)[CH2:17][O:18][Si](C(C)(C)C)(C)C)(C)(C)C>C(Cl)Cl>[NH2:43][C:16]([CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:32]=2)[CH2:27]1)([CH2:17][OH:18])[CH2:15][O:14][P:13](=[O:12])([OH:47])[OH:52]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67246851HCID 67246851, compound

Product 1

HCID 67247178HCID 67247178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-1 solution of trifluoro acetic acid and CH2Cl2 was added 14 (10 mg, 0.015 mmol). The reaction was left to stir for 3 hours. When reaction complete, product was concentrated and repeatedly co-evaporated with diethyl ether (5×10 mL) to remove TFA. The product could not be purified by column chromatography. Diethyl ether was added to bring the product into solution, followed by the addition of hexanes to precipitate out product 15. The precipitate was then washed with water to remove ionic impurities and then concentrated.

Workup

  1. waitThe reaction was left
  2. customWhen reaction complete
  3. concentrationproduct was concentrated
  4. customto remove TFA
  5. customThe product could not be purified by column chromatography
  6. additionDiethyl ether was added
  7. additionfollowed by the addition of hexanes
  8. customto precipitate out product 15
  9. washThe precipitate was then washed with water
  10. customto remove ionic impurities
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b73f18ea60644386a98f85bc2455bc88
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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