Ammonia → HCID 10193371, compound

HRID 1991249Notes

Reaction equation

HRID 1991249 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-c0016da35de4428c85eaa94929794b85
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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