Sodium Azide → HCID 86753887, compound

HRID 1418654Notes

Reaction equation

HRID 1418654 reaction equation
[F:1][CH2:2][CH2:3][N:4]([CH:6]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@@H:19]([CH2:21]CS([O-])(=O)=O)[O:18][C:17]3=[O:27])=[CH:12][C:11]=2[F:28])[CH2:7]1)[CH3:5].[N-:29]=[N+:30]=[N-:31].[Na+].CO.C(Cl)(Cl)Cl.S([O-])(=O)(=O)C>CN(C)C=O>[F:1][CH2:2][CH2:3][N:4]([CH:6]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@H:19]([CH2:21][N:29]=[N+:30]=[N-:31])[O:18][C:17]3=[O:27])=[CH:12][C:11]=2[F:28])[CH2:7]1)[CH3:5]

Participants

6

Reactant 4

HCID 33557Sodium Azide2×HCID 85257MethanesulfonateHCID 21584188Chloroform methanolHCID 86753888HCID 86753888, compound

Product 1

HCID 86753887HCID 86753887, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of (R)-[[3-[4-[3-[N-(2-fluoroethyl)-N-methylamino]-1-azetidinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (1.65 g, 3.94 mmol) in dry N,N-dimethylformamide (15 mL) was treated with solid sodium azide (0.768 g, 11.8 mmol). The reaction mixture was then heated to 65° C. under a nitrogen atmosphere. After 3 h, TLC analysis (5% methanol/chloroform) revealed a small amount of starting mesylate still remained. An additional portion of sodium azide (0.256 g, 3.94 mmol) was added and the reaction mixture heated at 65° C. for 1 h. The reaction mixture was cooled to ambient temperature, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (100 g), eluting with a gradient of 1-4% methanol/chloroform, to afford, after concentration of appropriate fractions, 1.24 g (86%) of the title compound as an off-white solid with mp 60°-63° C. and MS(EI) 366 (M+).

Workup

  1. temperaturethe reaction mixture heated at 65° C. for 1 h
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed over silica gel (100 g)
  6. washeluting with a gradient of 1-4% methanol/chloroform
  7. customto afford

Sources & evidence

ORD record
ord-d4040241d30a4362ba95979934cafa67
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

Loading…