2-Chloroethanol → HCID 54573174, compound

HRID 1078530Notes

Reaction equation

HRID 1078530 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.F[C:34](F)(F)[C:35](O)=[O:36].ClCCO.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[CH2:9][CH2:10][N:11]([CH2:34][CH2:35][OH:36])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 22875168HCID 22875168, compound

Product 1

HCID 54573174HCID 54573174, compoundYield 19%

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 (0.400 g, 0.881 mmol) in dichloromethane (3 mL) was treated with trifluoroacetic acid (7 mL) at room temperature for 1 h. The reaction mixture was concentrated in vacuo and the resultant amber syrup combined with 2-chloroethanol (354 μL, 5.27 mmol), potassium carbonate (0.730 g, 5.27 mmol), and acetonitrile (20 mL) and the mixture heated to reflux for 24 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was chromatographed over silica gel (10 g), eluting with 1%, 3%, and then 6% methanol/chloroform, to afford, after concentration of appropriate fractions, 0.067 g (19%) of the title compound as an off-white solid with mp 172°-174° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. temperaturethe mixture heated
  3. temperatureto reflux for 24 h
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed over silica gel (10 g)
  6. washeluting with 1%, 3%
  7. custom6% methanol/chloroform, to afford

Sources & evidence

ORD record
ord-979a1f8dc1434b2d82fcd0cef106e26f
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

Loading…