Sodium Bicarbonate → HCID 68452705, compound

HRID 2170523Notes

Reaction equation

HRID 2170523 reaction equation
C([O:4][C@@H:5]1[CH:10]=[CH:9][C@@:8]([OH:17])([C:11]#[C:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH2:7][O:6]1)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[OH:6][CH2:7][C:8]1([C:11]#[C:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[O:17][C@@H:5]([OH:4])[CH:10]=[CH:9]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68454631HCID 68454631, compound

Product 1

HCID 68452705HCID 68452705, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

400 mL of an aqueous solution containing 9.8 g of Lipase PS Amano SD was added to a solution of 98.4 g (387 mmol) of the acetylated form (Compound 5) dissolved in 300 mL of acetonitrile, and agitated at 40° C. overnight. At the end of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried with anhydrous sodium sulfate, filtrated, and subjected to vacuum concentration to obtain 84.2 g of a crude product (crude yield: 75.8%). The obtained crude product was subjected to column purification (n-Hex:AcOEt=3:1) to obtain 62.3 g of a mixture of Compounds 9 and 10 as a yellow oily product.

Workup

  1. customAt the end of the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltrated
  6. concentrationsubjected to vacuum concentration
  7. customto obtain 84.2 g of a crude product (crude yield: 75.8%)
  8. customThe obtained crude product
  9. customwas subjected to column purification (n-Hex:AcOEt=3:1)

Sources & evidence

ORD record
ord-d70c19fb929349868f964f0a4f64c25b
Source dataset
uspto-grants-2015_06
Patent number
US09051288B2

Reaction notes

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