Water → HCID 89975765, compound

HRID 1508626Notes

Reaction equation

HRID 1508626 reaction equation
Br.C(O)(=O)C.[Si:6]([O:23][C@@H:24]1[C@@H:28]([CH2:29][O:30][Si:31]([C:44]([CH3:47])([CH3:46])[CH3:45])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:27][CH:26]([O:48]C)[C@H:25]1[F:50])([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>C(Cl)Cl>[Si:6]([O:23][C@@H:24]1[C@@H:28]([CH2:29][O:30][Si:31]([C:44]([CH3:47])([CH3:46])[CH3:45])([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:27][CH:26]([OH:48])[C@H:25]1[F:50])([C:19]([CH3:21])([CH3:22])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 89975766HCID 89975766, compound

Product 1

HCID 89975765HCID 89975765, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 mL of 30% hydrogen bromide/acetic acid was added dropwise to a solution of 1.66 g of (3S,4R,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-fluoro-2-methoxyoxolane in 10 mL of methylene chloride at room temperature, and the obtained mixture was then stirred at room temperature for 3 hours. Thereafter, ethyl acetate and water were added to the reaction mixture, and the obtained mixture was then stirred for 5 minutes. Thereafter, the organic layer was fractionated, and it was washed with a 10% sodium hydrogen carbonate aqueous solution. After that, the solvent was distilled away under reduced pressure. 10 mL of acetonitrile and 10 mL of a 10% sodium hydrogen carbonate aqueous solution were added to the obtained residue, and the obtained mixture was then stirred at room temperature for 3 hours. Subsequently, the reaction mixture was left overnight. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and the solvent was then distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 9/1), so as to obtain 0.65 g of (3S,4R,5R)-4-((tert-butyldiphenylsilyl)oxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-3-fluorooxolan-2-ol in the form of a colorless oily product.

Workup

  1. stirringthe obtained mixture was then stirred for 5 minutes
  2. washit was washed with a 10% sodium hydrogen carbonate aqueous solution
  3. distillationAfter that, the solvent was distilled away under reduced pressure
  4. addition10 mL of acetonitrile and 10 mL of a 10% sodium hydrogen carbonate aqueous solution were added to the obtained residue
  5. stirringthe obtained mixture was then stirred at room temperature for 3 hours
  6. waitSubsequently, the reaction mixture was left overnight
  7. additionThereafter, ethyl acetate and water were added to the reaction mixture
  8. distillationthe solvent was then distilled away under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 9/1)

Sources & evidence

ORD record
ord-b270093b0b3a40c8a0042d5be4e0a391
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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