Water → HCID 68699508, compound

HRID 1026687Notes

Reaction equation

HRID 1026687 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-ad900ba0738a47a596fdf264ac05b7c9
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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