Water → HCID 68868318, compound

HRID 1988253Notes

Reaction equation

HRID 1988253 reaction equation
[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH:11]([CH2:31]OS(C)(=O)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:38]#[N:39].[K+].O>CS(C)=O>[CH2:1]([O:8][C:9](=[O:37])[NH:10][CH:11]([CH2:31][C:38]#[N:39])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([C:27]([CH3:28])([CH3:29])[CH3:30])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86760897HCID 86760897, compound

Product 1

HCID 68868318HCID 68868318, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(4-benzyloxy-3-t-butylphenyl)-1-methanesulfonyloxymethylethylcarbamic acid benzyl ester 1.93 g, 4.23 mmol) in DMSO (11 ml), potassium cyanide (827 mg, 12.7 mmol) was added and heated at 70° C. After stirring for 4 hours, the mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated to remove the solvent under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=2:1), giving the titled compound (1.42 g, 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-ef059b1fe4f54fcbbcfe21d345442dcb
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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