Methanol → HCID 131734115, compound

HRID 716127Notes

Reaction equation

HRID 716127 reaction equation
CO.Cl.CON.[Cl:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][O:13][C@@H:14]2[C@@H:18]([CH2:19][O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[O:17][CH:16]([OH:29])[C@H:15]2[F:30])=[CH:10][CH:9]=1.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:7][C:8]1[CH:32]=[CH:31][C:11]([CH2:12][O:13][C@H:14]([C@H:18]([OH:17])[CH2:19][O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[C@@H:15]([F:30])[CH:16]=[O:29])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 118108886HCID 118108886, compound

Product 1

HCID 131734115HCID 131734115, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a nitrogen atmosphere, 14 mL of methanol and 0.72 g of O-methylhydroxylamine hydrochloride were added to 2.89 g of (3S,4R,5R)-4-((4-chlorobenzyl)oxy)-5-(((4-chlorobenzyl)oxy)methyl)-3-fluorooxolan-2-ol, and thereafter, 1.21 mL of triethylamine was added dropwise to the mixture. The thus obtained mixture was stirred at room temperature for 12 hours. Thereafter, ethyl acetate was 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 50/50), so as to obtain 3.09 g of (2R,3R,4R)-3,5-bis((4-chlorobenzyl)oxy)-2-fluoro-4-hydroxypentanal=O-methyl=oxime in the form of a white solid.

Workup

  1. washthe thus obtained mixture was successively washed with water
  2. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium 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=90/10 to 50/50)

Sources & evidence

ORD record
ord-577acda1d5634a2dbc5715e2c6ccb829
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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