Acetonitrile → HCID 68452705, compound

HRID 2170525Notes

Reaction equation

HRID 2170525 reaction equation
C(#N)C.C([O:7][C@@H:8]1[CH:13]=[CH:12][C@@:11]([OH:20])([C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][O:9]1)(=O)C>O>[OH:9][CH2:10][C:11]1([C:14]#[C:15][Si:16]([CH3:17])([CH3:18])[CH3:19])[O:20][C@@H:8]([OH:7])[CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 68454631HCID 68454631, compound

Product 1

HCID 68452705HCID 68452705, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

570 mL of an acetonitrile solution containing 190 g of Compound 5 was heated to 40° C., to which 760 mL of an aqueous solution containing 19 g Lipase PS Amano SD was added and the resultant was agitated for 15 hours while maintaining the temperature at 40° C. After confirming the end of the reaction by thin-layer chromatography, the resultant was left to cool at room temperature, added with water and subjected to extraction with ethyl acetate. The organic layer was concentrated to obtain 148 g of a mixture of Compounds 9 and 10 as a clear brown oily product (crude yield: 93.8%).

Workup

  1. additioncontaining 19 g Lipase PS Amano SD
  2. additionwas added
  3. customthe end of the reaction by thin-layer chromatography
  4. waitthe resultant was left
  5. temperatureto cool at room temperature
  6. extractionsubjected to extraction with ethyl acetate
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-aefff3344e4f485eb3907a84572ea7fb
Source dataset
uspto-grants-2015_06
Patent number
US09051288B2

Reaction notes

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