Bromoacetonitrile → HCID 10429088, compound

HRID 456800Notes

Reaction equation

HRID 456800 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[N:10][NH:11][CH:12]=1.[H-].[Na+].Br[CH2:28][C:29]#[N:30]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[N:10][N:11]([CH2:28][C:29]#[N:30])[CH:12]=1

Participants

6

Reactant 3

HCID 11534Bromoacetonitrile2×HCID 24758Sodium hydrideHCID 178519213HCID 178519213, compound

Product 1

HCID 10429088HCID 10429088, compoundYield 108.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-[3-Fluoro-4-(1H-1,2,3-triazol4-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 7, 1.5 g, 4.6 mmol) was stirred in N,N-dimethylformamide at 0° C. Sodium hydride (0.35 g, 9.2 mmol) was added and the mixture was stirred 30 minutes. Bromoacetonitrile (0.66 g, 5.5 mmol) was added and the reaction was stirred overnight, slowly warming to room temperature. Starting material was present so additional bromoacetonitrile (0.33 g, 2.8 mmol) was added and the reaction was stirred for two additional days. The mixture was diluted with water and extracted using ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under vacuum to give a yellow solid (1.84 g). The solid was dissolved in dimethylsulfoxide (18 ml) and water (5 ml) and the isomers were separated using Gilson HPLC. Peaks 1 and 2 were collected, concentrated and lyophilized to give a light yellow solid (Example 10, peak 1, 36 mg; Example 11, peak 2, 182 mg). NOE experiments were used to distinguish the two isomers with the cyano group of peaks 1 and 2 corresponding to the 1 and 2 positions of the nitrogen, respectively.

Workup

  1. stirringthe reaction was stirred overnight
  2. additionwas added
  3. stirringthe reaction was stirred for two additional days
  4. extractionextracted
  5. washThe organic layer was washed with water
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e3022aead0124ad6b56bbc738e05bc63
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

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