Dimethylformamide → HCID 11383720, compound

HRID 1026673Notes

Reaction equation

HRID 1026673 reaction equation
[O:1]1[C:3]2([CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][C:12]([N:15]4[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]4=[O:25])=[CH:11][C:10]=3[F:26])[CH2:5][CH2:4]2)[CH2:2]1.[C-]#N.[K+].[CH3:30][N:31](C)C=O>CO>[C:30]([CH2:2][C:3]1([OH:1])[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][C:16]3=[O:25])=[CH:11][C:10]=2[F:26])[CH2:5][CH2:4]1)#[N:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 11382912HCID 11382912, compound

Product 1

HCID 11383720HCID 11383720, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by reacting (S)—N-{3-[4-(1-oxa-6-aza-spiro[2.5]oct-6-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (18.0 mmol) and potassium cyanide (22.0 mmol) in methanol: dimethylformamide mixture (1:5, 20 ml) at a temperature 25° C. for 14 hours and by purifying the compound by silica gel column chromatography in 51% yield.

Workup

  1. customby purifying the compound by silica gel column chromatography in 51% yield

Sources & evidence

ORD record
ord-ed774d3e680740279bb9f43dfecf3245
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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