Lithium azide → HCID 18642953, compound

HRID 263698Notes

Reaction equation

HRID 263698 reaction equation
[Si:1]([O:8][C:9]([C:11]([F:35])([F:34])[C@:12](OS(C(F)(F)F)(=O)=O)([C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])O)=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:36]=[N+:37]=[N-:38].[Li+]>CN(C)C=O>[Si:1]([O:8][C:9]([C:11]([F:35])([F:34])[C@H:12]([N:36]=[N+:37]=[N-:38])[C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 18642954HCID 18642954, compound

Product 1

HCID 18642953HCID 18642953, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4.53 g (8.7 mmol) 1-t-butyldimethylsilyloxy-5-benzoyl-3-trifluoromethanesulfonyloxy-2-deoxy-2,2-difluoroxylose in dimethylformamide (50 ml) were added 1.2 g (25.2 mmol) lithium azide and the reaction mixture was heated at 70° C. for 40 minutes. The reaction mixture was then concentrated under reduced pressure and the residue dissolved in ethyl acetate. This solution was washed several times with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was redissolved in a small amount of ethyl acetate and poured over a pad of silica gel, eluting with ethyl acetate. The filtrates were concentrated under reduced pressure to give 2.09 g (58%) of the desired compound as a colorless oil. FD-MS: m/e=356, (M-57, loss of t-butyl), 357((M+1)-57, loss of t-butyl). IR(neat): 2114 cm-1, N3.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThis solution was washed several times with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was redissolved in a small amount of ethyl acetate
  7. additionpoured over a pad of silica gel
  8. washeluting with ethyl acetate
  9. concentrationThe filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-080b8d7cb99d41679c2ab4a077f8afa9
Source dataset
uspto-grants-1997_07
Patent number
US05644043

Reaction notes

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