Potassium Carbonate → HCID 18684832, compound

HRID 277804Notes

Reaction equation

HRID 277804 reaction equation
[Cl:1][CH:2]([Cl:33])[C:3]([NH:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:31])[CH2:26][O:27]C(=O)C)[CH2:21][CH2:20]3)=[C:15]([F:32])[CH:14]=2)[CH2:8]1)=[O:4].C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:33][CH:2]([Cl:1])[C:3]([NH:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:20][CH2:21][N:22]([C:25](=[O:31])[CH2:26][OH:27])[CH2:23][CH2:24]3)=[C:15]([F:32])[CH:14]=2)[CH2:8]1)=[O:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 54419963HCID 54419963, compound

Product 1

HCID 18684832HCID 18684832, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-(−)-2,2-dichloro-N-[[2-oxo-3-[3-fluoro-4-[1-[(acetoxy)acetyl]-4-piperidinyl]phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 32, 110 mg) and anhydrous potassium carbonate (60 mg) in methanol (8.8 mL) is stirred under N2 at ambient temperature for one hour and then concentrated under reduced pressure and chromatographed on silica gel (70-230 mesh, 10 g), eluting with methanol/chloroformn (10/90). Pooling and concentration of those fractions with an Rf=0.41 by TLC (methanol/chloroform, 10/90), repurification by radial chromatography (2000 m silica gel plate) eluting with methanol/methylene chloride, and trituration with chloroform/diethyl ether gives the title compound, NMR (CDCl3, 400 MHz) 7.46, 7.39, 7.15, 5.99, 4.84, 4.74, 4.22, 4.09, 3.77, 3.61, 3.10, 2.79, 1.89, 1.65δ.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed on silica gel (70-230 mesh, 10 g)
  3. washeluting with methanol/chloroformn (10/90)
  4. customPooling and concentration of those fractions with an Rf=0.41 by TLC (methanol/chloroform, 10/90), repurification by radial chromatography (2000 m silica gel plate)
  5. washeluting with methanol/methylene chloride, and trituration with chloroform/diethyl ether

Sources & evidence

ORD record
ord-3ea6429d8ab145ab84d8a2f42723dc65
Source dataset
uspto-grants-2002_03
Patent number
US06358942B1

Reaction notes

Loading…