Allylamine → HCID 10193592, compound

HRID 1826191Notes

Reaction equation

HRID 1826191 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[F:5][C:6]1[CH:7]=[C:8]([N:18]2[CH2:22][C@H:21]([C:23](Cl)=[O:24])[O:20][C:19]2=[O:26])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O1CCCC1.O>[F:5][C:6]1[CH:7]=[C:8]([N:18]2[CH2:22][C@H:21]([C:23]([NH:4][CH2:1][CH:2]=[CH2:3])=[O:24])[O:20][C:19]2=[O:26])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 23730107HCID 23730107, compound

Product 1

HCID 10193592HCID 10193592, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a flame-dried flask under nitrogen was added allylamine (0.60 mL, 8.05 mmol). The flask was cooled in an ice bath, and a solution of (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarbonyl chloride (EXAMPLE 435, Step 2, 0.805 mmol theory) in anhydrous tetrahydrofuran (8.0 mL) was added. The resulting mixture was stirred under nitrogen for 2 hours, allowing the cooling bath to slowly expire, and was then diluted with water (10 mL) and extracted with methylene chloride (20 mL). The organic phase was washed with water (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of methanol/methylene chloride (0.5/99.5-2/98). Pooling and concentration of those fractions with an Rf=0.44 by TLC (methanol/chloroform, 5/95) provides the title compound, mp 167-169° C.; MS (ESI+) for C17H20FN3O4 m/z 350 (M+H)+; [α]25D=−44° (c 0.94, DMSO).

Workup

  1. temperatureThe flask was cooled in an ice bath
  2. extractionextracted with methylene chloride (20 mL)
  3. washThe organic phase was washed with water (10 mL) and saline (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe crude product was chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  7. washeluting with a gradient of methanol/methylene chloride (0.5/99.5-2/98)

Sources & evidence

ORD record
ord-738d933b364f40c695decd1f8c764b0e
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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