Sodium Bicarbonate → HCID 20726135, compound

HRID 1378694Notes

Reaction equation

HRID 1378694 reaction equation
Cl.[CH3:2][NH2:3].[F:4][C:5]1[CH:6]=[C:7]([N:18]2[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[H][H].C(=O)([O-])O.[Na+]>[Pd].CO.C(Cl)Cl>[F:4][C:5]1[CH:6]=[C:7]([N:18]2[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:8]=[CH:9][C:10]=1[N:11]1[CH2:12][CH2:13][CH:14]([NH:3][CH3:2])[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 6364545Methylamine hydrochlorideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 20726135HCID 20726135, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

Methylamine hydrochloride (0.46 g) and palladium on carbon (0.20 g) were added to a methanol-methylene chloride solution (20-20 ml) of 2.00 g of the (S)-N-{3-[3-fluoro-4-(4-oxo-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 7) which was synthesized in Example 3, and the mixture was stirred at room temperature for 14 h under 2 atm hydrogen atmosphere. Sodium hydrogencarbonate was added and the mixture was stirred for 10 min. Thereafter, the catalyst was filtered off and the solvent was evaporated under vacuum. The residue was purified by alumina column chromatography (solvent: chloroform/methanol=100/1-30/1) to afford the title compound (900 mg) in a yield of 43%.

Workup

  1. custom7) which was synthesized in Example 3
  2. filtrationThereafter, the catalyst was filtered off
  3. customthe solvent was evaporated under vacuum
  4. customThe residue was purified by alumina column chromatography (solvent: chloroform/methanol=100/1-30/1)

Sources & evidence

ORD record
ord-2e7d3c44b11a463dacb863a372a20da3
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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