Water → HCID 68699508, compound

HRID 2247035Notes

Reaction equation

HRID 2247035 reaction equation
O=[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+].[Cl-].[NH4+:30].O>C(O)(=O)C>[NH2:30][C:2]1([C:26]#[N:27])[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

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 68699508HCID 68699508, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (S)-N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.0 mmol), potassium cyanide (1.3 mmol) and ammonium chloride (10 mmol) in acetic acid (10 ml) was stirred for 14 hours at a temperature 25° C. The reaction mixture was pored in the water and was extracted with chloroform. Evaporation of solvent and silica gel column chromatographic purification of the residue afforded the title compound in 65% yield.

Workup

  1. extractionwas extracted with chloroform
  2. customEvaporation of solvent and silica gel column chromatographic purification of the residue

Sources & evidence

ORD record
ord-31f59e88d31d484792cfb6ee2dbbdc30
Source dataset
uspto-grants-2010_03
Patent number
US07687627B2

Reaction notes

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