Potassium Cyanide → (S)-N-{3-[4-(4-cyano-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1026671Notes

Reaction equation

HRID 1026671 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.[C-:26]#[N:27].[K+]>CN(C)C=O>[C:26]([C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:6][CH2:7]1)#[N:27]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 11394757(S)-N-{3-[4-(4-cyano-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by reacting (S)—N-{3-[4-(4-oxopiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (12.0 mmol) and potassium cyanide (18.0 mmol) in dimethylformamide (25 ml) at a temperature 25° C. for four hours and by purifying the compound by silica gel column chromatography in 42% yield.

Workup

  1. customat a temperature 25° C.
  2. customfor four hours
  3. customby purifying the compound by silica gel column chromatography in 42% yield

Sources & evidence

ORD record
ord-0aeed65cba8a472ab77341104584719e
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

Loading…