Methylamine → HCID 10215354, compound

HRID 896131Notes

Reaction equation

HRID 896131 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.[CH3:28][NH2:29]>CO>[CH3:28][NH:29][C:20]([C@@H:18]1[O:17][C:16](=[O:27])[N:15]([C:4]2[CH:3]=[C:2]([F:1])[C:7]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[C:6]([F:14])[CH:5]=2)[CH2:19]1)=[O:21]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23730109HCID 23730109, compound

Product 1

HCID 10215354HCID 10215354, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The butyl (5R)-3-[3,5-difluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinecarboxylate (EXAMPLE 17, Step 1) is treated with 2M methylamine in MeOH (0.1 M in starting material), and the reaction mixture is stirred at ambient temperature for 30 mins and then concentrated under reduced pressure. The residue is purified by radial chromatography [4000 micron silica gel rotor; MeOH/CH2Cl2 (3/97) eluent] to give the title compound, mp 179-181° C.; MS (ESI+) for C15H17N3O4F2 m/z 342 (M+H)+; [α]25D−40 (c 0.95, DMSO).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by radial chromatography [4000 micron silica gel rotor; MeOH/CH2Cl2 (3/97) eluent]

Sources & evidence

ORD record
ord-d7e0f3ed490a4583b23753f28fd30bc3
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

Loading…