Boron Trichloride → HCID 86751721, compound

HRID 1939711Notes

Reaction equation

[N:1]([CH2:4][C@@H:5]([O:15][O:16][C:17]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[P:18]([OH:21])([OH:20])=[O:19])[CH2:6][O:7]CC1C=CC=CC=1)=[N+:2]=[N-:3].B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]([CH2:4][C@@H:5]([O:15][O:16][C:17]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:23])[CH3:24])[P:18]([OH:20])([OH:21])=[O:19])[CH2:6][OH:7])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: -78 °C

Procedure

(R)-3-Azido-1-O-benzyl-2-O-(diisopropyl phosphonomethoxyl)-1,2-propanediol (6.15 g, 15.96 mmol) was dissolved in 35 mL of anhydrous methylene chloride under nitrogen atmosphere. To this solution, boron trichloride (1M in methylene chloride) (48 mL, 48 mmol) was slowly added at -78° C. The mixture was stirred at -78° C. for 4 hour, and then saturated aqueous sodium bicarbonate (100 mL) and methylene chloride (150 mL) were added. The aqueous layer was separated and extrated with methylene chloride (150 mL×2). The combined methylene chloride extracts were dried over magnesium sulfate. Filtration and concentration under reduced pressure gave a residue which was purified by flash chromatography on silica gel (methylene chloride:acetone=5:1 to 1:1) to provide 4.39 q (93% yield) of the title compound as an oil.

Workup

customThe aqueous layer was separated
dry with materialThe combined methylene chloride extracts were dried over magnesium sulfate
filtrationFiltration and concentration under reduced pressure
customgave a residue which
customwas purified by flash chromatography on silica gel (methylene chloride:acetone=5:1 to 1:1)

Sources & evidence

ORD record: ord-34147dd96e0a43ab86bdd068d3030ade
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696263

Reaction notes

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