Trifluoroacetic acid → HCID 66805370, compound

HRID 1193256Notes

Reaction equation

HRID 1193256 reaction equation
C(O)(C(F)(F)F)=O.C(OC([N:15]([CH2:29][CH3:30])[C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl>[CH2:29]([NH:15][C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1)[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66798910HCID 66798910, compound

Product 1

HCID 66805370HCID 66805370, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (25 ml) was added dropwise at 0° C. to a solution of (R)-methyl 3-(tert-butoxycarbonyl-(ethyl)amino)-2,3-dihydro-1H-indene-5-carboxylate (10.84 g, 33.97 mmol, 1 eq) in DCM (100 ml), and the mixture was stirred for 1 hour at RT. After monitoring by TLC, the reaction solution was concentrated under reduced pressure, the residue was taken up in sat. sodium hydrogen carbonate solution (500 ml) and extraction with ethyl acetate (3×1000 ml) was carried out. The combined org. phases were washed with sat. sodium chloride solution (800 ml), dried over sodium sulfate, concentrated and used in the following stage without being purified further. The desired product was in the form of a light-brown liquid. Yield: 91% (6.8 g, 31.05 mmol)

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextraction with ethyl acetate (3×1000 ml)
  3. washphases were washed with sat. sodium chloride solution (800 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customwithout being purified further

Sources & evidence

ORD record
ord-dee8c03848cf427b86fb1ba1f5732110
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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