Trifluoroacetic acid → HCID 21226950, compound

HRID 1940656Notes

Reaction equation

HRID 1940656 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:5]=[C:6]([F:21])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.FC(F)(F)C(O)=O.[CH3:40][O:41][CH2:42][CH2:43]Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(#N)C>[F:21][C:6]1[CH:5]=[C:4]([N:22]2[CH2:26][C@H:25]([CH2:27][NH:28][C:29](=[O:31])[CH3:30])[O:24][C:23]2=[O:32])[CH:3]=[C:2]([F:1])[C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:43][CH2:42][O:41][CH3:40])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 22875168HCID 22875168, compound

Product 1

HCID 21226950HCID 21226950, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-N-[[3-[3,5-difluoro-4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (0.200 g, 0.441 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (4 mL) at room temperature for 1 h. The reaction mixture was concentrated in vacuo and the resultant residue combined with 2-chloroethyl methyl ether (403 μL, 4.41 mmol), potassium carbonate (0.730 g, 5.28 mmol), and acetonitrile (9 mL) and the mixture heated to reflux for 15 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was triturated with dichloromethane, the solids filtered off, and the filtrate concentrated in vacuo to give the crude product. This crude material was chromatographed over silica gel (10 g), eluting with 1%, 3%, and then 5% methanol/chloroform, to afford, after concentration of appropriate fractions, 0.097 g (53%) of the title compound as an off-white solid with mp 162°-164° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. temperaturethe mixture heated
  3. temperatureto reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with dichloromethane
  6. filtrationthe solids filtered off
  7. concentrationthe filtrate concentrated in vacuo
  8. customto give the crude product
  9. customThis crude material was chromatographed over silica gel (10 g)
  10. washeluting with 1%, 3%
  11. custom5% methanol/chloroform, to afford

Sources & evidence

ORD record
ord-cc142100ba454f9bb5925040bf6b78ed
Source dataset
uspto-grants-1997_12
Patent number
US05700799

Reaction notes

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