Sodium Cyanide → HCID 68653325, compound

HRID 499701Notes

Reaction equation

HRID 499701 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:22])([CH3:21])[CH2:15]OS(C)(=O)=O)[CH2:11][O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:25]#[N:26].[Na+]>CS(C)=O.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:22])([CH3:21])[CH2:15][C:25]#[N:26])[CH2:11][O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 86630100HCID 86630100, compound

Product 1

HCID 68653325HCID 68653325, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2.04 g of 4(S)-(3-methanesulfonyloxy-2,2-dimethyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester and 2.17 g of sodium cyanide in 12 ml of dimethylsulfoxide is heated to 135° C. for 15 hours. The mixture is cooled to room temperature and diluted with water and ethyl acetate. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.32 (1:1 EtOAc-heptane); Rt=4.82 (gradient I).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate
  4. dry with materialThe combined organic layers are dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37dbe570c99248c1af89a11f0667b0c3
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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