Trifluoroacetic acid → HCID 54042469, compound

HRID 277806Notes

Reaction equation

HRID 277806 reaction equation
C1(COC([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:22]([F:23])=[CH:21][C:20]([N:24]4[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]4=[O:34])=[CH:19][C:18]=3[F:35])[CH2:13][CH2:12]2)=O)C=CC=CC=1.FC(F)(F)C(O)=O>>[O:34]=[C:25]1[N:24]([C:20]2[CH:19]=[C:18]([F:35])[C:17]([CH:14]3[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)=[C:22]([F:23])[CH:21]=2)[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69766454HCID 69766454, compound

Product 1

HCID 54042469HCID 54042469, compound

Conditions

Temperature
0 °C

Procedure

A mixture of (S)-(−)-4-[4-[5-[(acetylamino)methyl]-2-oxo-3-oxazolidinyl]-2,6-difluorophenyl]-1-piperidinecarboxylic acid phenylmethyl ester ((EXAMPLE 35, Step 7, 847 mg) and trifluoroacetic acid (12 mL) maintained at 0° C. under N2 is stirred for two hours and then concentrated under reduced pressure to remove excess trifluoroacetic acid. The residue is diluted with saturated aqueous potassium carbonate (70 mL) and methylene chloride (50 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (2×50 mL), and the combined organic phase is dried over anhydrous sodium sulfate, concentrated under reduced pressure, triturated with diethyl ether and recrystallized from ethyl acetate to give the title compound, NMR (CDCl3, 400 MHz) 7.08, 6.10, 4.78, 4.00, 3.74, 3.64, 3.19, 3.07, 2.72, 2.03, 1.99, 1.68δ.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove excess trifluoroacetic acid
  3. additionThe residue is diluted with saturated aqueous potassium carbonate (70 mL) and methylene chloride (50 mL)
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted with methylene chloride (2×50 mL)
  6. dry with materialthe combined organic phase is dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customtriturated with diethyl ether
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3d2ce09a7ef94f35ad1b9cccac11f0a1
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

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