Hydrochloric Acid → HCID 89975649, compound

HRID 1508616Notes

Reaction equation

HRID 1508616 reaction equation
C=O.Cl.CON=C[C@H:8]([F:33])[C@H:9]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C@@H:10]([Br:22])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[C:34](=O)([O-])[OH:35].[Na+]>CC(C)=O.C(OCC)(=O)C>[Br:22][C@@H:10]([CH2:11][O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[C@@H:9]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C@H:8]([F:33])[CH:34]=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 131734114HCID 131734114, compound

Product 1

HCID 89975649HCID 89975649, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.2 mL of a 35% formaldehyde solution and 4.2 mL of 2 mol/L hydrochloric acid were added to a solution of 857 mg of (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)pentanal O-methyloxime in 17 mL of acetone at room temperature, and the obtained mixture was then stirred at room temperature for 1.75 hours. Thereafter, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 60/40), so as to obtain 598 mg of colorless oily (2S,3S,4S)-4-bromo-2-fluoro-3,5-bis((4-methoxybenzyl)oxy)pentanal and a water adduct thereof.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous sodium sulfate
  3. distillationAfter that, the solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 to 60/40)

Sources & evidence

ORD record
ord-1d4bd508d7a44d30a84e82a13fbf7706
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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