Ammonia → HCID 10193371, compound

HRID 1826206Notes

Reaction equation

HRID 1826206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([C:20](OCCCC)=[O:21])[O:17][C:16]2=[O:27])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[NH3:28]>CO>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([C:20]([NH2:28])=[O:21])[O:17][C:16]2=[O:27])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23730109HCID 23730109, compound

Product 1

HCID 10193371HCID 10193371, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The butyl (SR)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 350 mg, 0.910 mmol) was treated with 7N ammonia in methanol (9.1 mL) under N2, and the mixture was stirred at ambient temperature for 30 mins. The reaction mixture was then concentrated under reduced pressure, and the residue was recrystallized from EtOAc/hexanes to give the title compound, mp 181-183° C.; MS (ESI+) for C14H15N3O4F2 m/z 328 (M+H)+; [α]25D −23 (c 0.94, DMSO).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-336edcdd067040c8b3fa6ad0c2b1b5cb
Source dataset
uspto-grants-2006_05
Patent number
US07049443B2

Reaction notes

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