Ammonia → HCID 9944468, compound

HRID 1991248Notes

Reaction equation

HRID 1991248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19](OCC)=[O:20])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[NH3:25]>CO>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([C:19]([NH2:25])=[O:20])[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86590830ethyl (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate

Product 1

HCID 9944468HCID 9944468, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl (5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 0.22 g, 0.65 mmol) in 2M ammonia in methanol (5-6 mL) is heated in a closed vial at 60° C. for approximately 1 h. The resulting mixture is cooled to ambient temperature and concentrated under reduced pressure, and the crude product is recrystallized from methanol to give the title compound, MS (ESI+) for C14H16N3O4F m/z 310 (M+H)+.

Workup

  1. temperatureThe resulting mixture is cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customthe crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-849320abd45c4ec384a4886b5c66d431
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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