Ethanamine, 2-fluoro-, hydrochloride → HCID 10286694, compound

HRID 896127Notes

Reaction equation

HRID 896127 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@H:14]([C:16]([O:18]CCCC)=O)[O:13][C:12]3=[O:23])=[CH:10][C:5]=2[S:4][C:3]1=[O:24].Cl.[F:26][CH2:27][CH2:28][NH2:29]>N1C=CC=CC=1.C(Cl)Cl>[F:26][CH2:27][CH2:28][NH:29][C:16]([C@@H:14]1[O:13][C:12](=[O:23])[N:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[C:3](=[O:24])[S:4][C:5]=3[CH:10]=2)[CH2:15]1)=[O:18]

Participants

5

Reactant 2

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 68489799HCID 68489799, compound

Product 1

HCID 10286694HCID 10286694, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of butyl (5R)-3-(2,3-dihydro-3-methyl-2-oxo-6-benzothiazolyl)-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 29, Step 2, 985 mg, 2.81 mmol) in pyridine (5.5 mL) in a thick-walled, screw-cap vial is treated with fluoroethylamine hydrochloride (2.20 g, 22.1 mmol), and the stirred reaction mixture is placed in an oil bath maintained at 90° C. for 24 h. The mixture is then cooled to ambient temperature, diluted with CH2Cl2 (50 mL), washed with 0.2 M hydrochloric acid (25 mL portions, until the washings are at pH<2) and saline (25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is chromatographed on a Flash 40M 90 g silica gel cartridge with MeOH/CH2Cl2 (1/99-2.5/97.5). Those fractions with an Rf=0.32 by TLC (MeOH/CHCl3, 5/95) are pooled and concentrated and the residue triturated and filtered from MeOH to give the title compound, mp 201-203° C.; MS (ESI−) for C14H14N3O4FS m/z 338 (M−H)−.

Workup

  1. customthe stirred reaction mixture
  2. customis placed in an oil bath
  3. temperatureThe mixture is then cooled to ambient temperature
  4. washwashed with 0.2 M hydrochloric acid (25 mL portions
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue is chromatographed on a Flash 40M 90 g silica gel cartridge with MeOH/CH2Cl2 (1/99-2.5/97.5)
  8. concentrationconcentrated
  9. customthe residue triturated
  10. filtrationfiltered from MeOH

Sources & evidence

ORD record
ord-e1884afdc4b24e38b5b059b60b212f3d
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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