Acetic Acid → HCID 118108886, compound

HRID 1508622Notes

Reaction equation

HRID 1508622 reaction equation
C(O)(=O)C.O.S(=O)(=O)(O)O.[Cl:11][C:12]1[CH:37]=[CH:36][C:15]([CH2:16][O:17][C@H:18]2[C@H:22]([F:23])[CH:21]([O:24]C)[O:20][C@@H:19]2[CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:14][CH:13]=1>CCCCCC.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C@@H:18]2[C@@H:19]([CH2:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[O:20][CH:21]([OH:24])[C@H:22]2[F:23])=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric Acid2×HCID 89975644HCID 89975644, compound

Product 1

HCID 118108886HCID 118108886, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

27 mL of acetic acid, 6.6 mL of water and 1.06 mL of concentrated sulfuric acid were added to 3.32 g of (2R,3R,4S)-3-((4-chlorobenzyl)oxy)-2-(((4-chlorobenzyl)oxy)methyl)-4-fluoro-5-methoxyoxolane, and the obtained mixture was then stirred at 70° C. for 2 hours. Thereafter, 4.5 mL of water and 0.53 mL of concentrated sulfuric acid were added to the reaction mixture, and the obtained mixture was then stirred at 70° C. for 5 hours. Thereafter, ethyl acetate and hexane were added to the reaction mixture, and the thus obtained mixture was successively washed with water and a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 30/70), so as to obtain 2.92 g of (3S,4R,5R)-4-((4-chlorobenzyl)oxy)-5-(((4-chlorobenzyl)oxy)methyl)-3-fluorooxolan-2-ol in the form of a colorless oily product.

Workup

  1. stirringthe obtained mixture was then stirred at 70° C. for 5 hours
  2. washthe thus obtained mixture was successively washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate
  4. distillationAfter that, the solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 30/70)

Sources & evidence

ORD record
ord-a868e15ccbae418ea971bf9ffd7cda0d
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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