Trifluoroacetic acid → HCID 68223934, compound

HRID 1400957Notes

Reaction equation

HRID 1400957 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH3:19])[CH2:5][N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:19][C@H:4]([CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[C:3]([O:2][CH3:1])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25418686HCID 25418686, compound

Product 1

HCID 68223934HCID 68223934, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 565 (523 mg, 1.83 mmol) and TFA (5 ml) in DCM (15 ml) was stirred at rt for 3.5 h. The reaction mixture was concentrated (azeotropes with DCM), diluted with water, stirred for 10 min, and the pH was adjusted to around 9 with a saturated aqueous solution of sodium bicarbonate and 1N NaOH. The alkaline solution was extracted with DCM; the extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under high vacuum to afford the desired product 566 (314 mg, 1.68 mmol, 92% yield) as a yellow oil that was used crude in the next step without any further purification. MS (m/z): 187.2 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated (azeotropes with DCM)
  2. additiondiluted with water
  3. extractionThe alkaline solution was extracted with DCM
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-e7dc501129904413badaae28f5c708d8
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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