2-Chloroethanol → HCID 54573174, compound

HRID 1940658Notes

Reaction equation

HRID 1940658 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-fbac3660e685429cb0c7e21ba97113c2
Source dataset
uspto-grants-1997_12
Patent number
US05700799

Reaction notes

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