Potassium Cyanide → HCID 86599012, compound

HRID 1026686Notes

Reaction equation

HRID 1026686 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][C:3]1([CH3:27])[CH3:26].[C-:28]#[N:29].[K+]>CN(C)C=O>[C:28]([C:2]1([OH: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][C:3]1([CH3:27])[CH3:26])#[N:29]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 59754027HCID 59754027, compound

Product 1

HCID 86599012HCID 86599012, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By reacting (S)—N-{3-[4-(4-oxo-3,3-dimethyl-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.40 mmol) and potassium cyanide (2.6 mmol) in dimethylformamide (10 ml) followed by silica gel chromatographic separation of diastereomer the compound was obtained in 78% yield. M.P. 65-68° C. and MS (M+1)=405 (MH+, 100%) for M.F.=C20H25FN4O4.

Workup

  1. customfollowed by silica gel chromatographic separation of diastereomer the compound
  2. customwas obtained in 78% yield

Sources & evidence

ORD record
ord-108e6b8890714fcab6160158c18db969
Source dataset
uspto-grants-2014_05
Patent number
US08729269B2

Reaction notes

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