Acetate → HCID 53840423, compound

HRID 2256472Notes

Reaction equation

HRID 2256472 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:22])([CH2:16][O:17]C(=O)CC)[CH2:10][O:11][C:12](=[O:15])[CH2:13][CH3:14].C([O-])(=O)C>C1CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:22])([CH2:10][O:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 175AcetateHCID 15463463HCID 15463463, compound

Product 1

HCID 53840423HCID 53840423, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

A 200 ml reaction vessel was charged with 3 g of 2-(2,4-difluorophenyl)-1,3-dipropionyloxy-2-propanol, 200 mg of Lipase D made by Amano Pharmaceutical Co., Ltd. (derived from Rhizpus delemer, Enzyme No. 6), 100 ml of 50 mM acetate buffer (pH 5) and 10 ml of cyclohexane. The resulting mixture was stirred at 30° C. to react for 18 hours. After the reaction liquid was extracted three times with 50 ml of ethylacetate, the organic layers were combined and the combined organic layer was washed with saturated aqueous solution with sodium bicarbonate and with saturated aqueous solution with sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed trader reduced pressure and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give 1.55 g of oily (R)-2-(2,4-difluorophenyl)-3-propionyloxy-1,2-propanediol. An optical purity thereof was determined in the same manner as in Example 35. (Elution time: 16.7 minutes ((R)-form) and 13.5 minutes ((S)-form)).

Workup

  1. customA 200 ml reaction vessel
  2. customto react for 18 hours
  3. customAfter the reaction liquid
  4. extractionwas extracted three times with 50 ml of ethylacetate
  5. washthe combined organic layer was washed with saturated aqueous solution with sodium bicarbonate and with saturated aqueous solution with sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed trader reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-884ea3c016d84c77bae0b1824a2ee547
Source dataset
uspto-grants-1997_08
Patent number
US05654472

Reaction notes

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