Ammonia → HCID 10193371, compound

HRID 896113Notes

Reaction equation

HRID 896113 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 (5R)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (Step 1, 350 mg, 0.910 mmol) is treated with 7N ammonia in methanol (9.1 mL) under N2, and the mixture is stirred at ambient temperature for 30 mins. The reaction mixture is then concentrated under reduced pressure, and the residue is 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 is then concentrated under reduced pressure
  2. customthe residue is recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-29bf0984b47d4e5e8ffee6965d34b5e0
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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