Sodium Hydroxide → HCID 66917185, compound

HRID 1034577Notes

Reaction equation

HRID 1034577 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[C:8](=[O:20])[CH2:9][C@@H:10]([O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:11]=1)=[O:5])C.[OH-].[Na+]>P([O-])([O-])([O-])=O>[OH:5][C:4]([CH2:6][C:7]1[C:8](=[O:20])[CH2:9][C@@H:10]([O:12][Si:13]([CH2:16][CH3:17])([CH2:18][CH3:19])[CH2:14][CH3:15])[CH:11]=1)=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24886194HCID 24886194, compound

Product 1

HCID 66917185HCID 66917185, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

20 g of (R)-2-ethoxycarbonylmethyl-4-triethylsilyloxy-2-cyclopenten-1-one obtained from Example 35 and 2 g of Candida antarcitica lipase were suspended in 200 ml of phosphate buffer (10 mM, pH 6.5-7.5) and stirred at room temperature. The pH of the solution was maintained by 1N sodium hydroxide solution and finally adjusted to 7.0 upon completion of the reaction and the Lipase was removed by filtration. The reaction mixture was extracted with 100 ml of ethyl acetate twice. The pH of the aqueous layer was further adjusted to 6.0 using a saturated sodium hydrogensulfate solution. The aqueous layer was extracted twice again using 100 ml of ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain (R)-2-hydroxycarbonylmethyl-4-triethylsiloxy-2-cyclopenten-1-one (12 g, 65% yield). [α]D: +19.8° (c 1.0, CH3CN);

Workup

  1. customfinally adjusted to 7.0 upon completion of the reaction
  2. customthe Lipase was removed by filtration
  3. extractionThe reaction mixture was extracted with 100 ml of ethyl acetate twice
  4. extractionThe aqueous layer was extracted twice again
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f3336c014dcc4a66b226a9c73d7fa9ff
Source dataset
uspto-grants-2013_10
Patent number
US08546114B2

Reaction notes

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