Potassium Carbonate → HCID 18684832, compound

HRID 1740157Notes

Reaction equation

HRID 1740157 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/chloroform (10/90). Pooling and concentration of those fractions with an Rf =0.41 by TLC (methanol/chloroform, 10/90), repurification by radial chromatography (2000μ 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, 1.65 δ.

Workup

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

Sources & evidence

ORD record
ord-ea59bcd9915941d19f2c9f6e93386f4a
Source dataset
uspto-grants-1999_10
Patent number
US05968962

Reaction notes

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