HCID 57085301, compound → HCID 57236480, compound

HRID 725129Notes

Reaction equation

HRID 725129 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][NH:7][C:8](=[O:22])[C@@H:9]([NH:18][C:19](=[O:21])[CH3:20])[CH2:10][O:11]C1CCCCO1)([O-:3])=[O:2]>Cl.O1CCOCC1>[N+:1]([O:4][CH2:5][CH2:6][NH:7][C:8](=[O:22])[C@@H:9]([NH:18][C:19](=[O:21])[CH3:20])[CH2:10][OH:11])([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 57085301HCID 57085301, compound

Product 1

HCID 57236480HCID 57236480, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

In 5 ml of 4N-hydrogen chloride/dioxane solution was dissolved 0.42 g of (2S)-N-(2-nitrooxyethyl)-2-acetylamino-3-(tetrahydropyran-2-yl)oxypropanamide, and the resulting solution was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the residue was neutralized with aqueous sodium hydrogencarbonate. The mixture was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography through silica gel using ethyl acetate as an eluent and recrystallized from ethyl acetate to give 48 mg of the title compound as colorless crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-50ecec5827e4437aa0570f2dfa4704d5
Source dataset
uspto-grants-1998_01
Patent number
US05705527

Reaction notes

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