Sodium Azide → HCID 15381193, compound

HRID 1418646Notes

Reaction equation

HRID 1418646 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@@H:17]([CH2:19]CS([O-])(=O)=O)[O:16][C:15]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:11][CH:10]([O:12][CH3:13])[CH2:9]1.[N-:26]=[N+:27]=[N-:28].[Na+].S([O-])(=O)(=O)C.CO.C(Cl)(Cl)Cl>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:26]=[N+:27]=[N-:28])[O:16][C:15]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:11][CH:10]([O:12][CH3:13])[CH2:9]1

Participants

6

Reactant 4

HCID 33557Sodium Azide2×HCID 85257MethanesulfonateHCID 21584188Chloroform methanolHCID 86753884HCID 86753884, compound

Product 1

HCID 15381193HCID 15381193, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

(R)-[[3-[3-fluoro-4-(3-methoxy-1-azetidinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]methanesulfonate (0.508 g, 1.36 mmol) was combined with sodium azide (0.106 g, 1.63 mmol) in N,N-dimethylformamide (4 mL). The reaction mixture was heated to 65° C. under a nitrogen atmosphere. After 2 hours, a small amount of the starting mesylate still remained by TLC analysis (5% methanol/chloroform). An additional 0.044 g of sodium azide was added and the reaction heated for a further 1.5 h, at which time TLC revealed the reaction to be complete. The reaction mixture was filtered and concentrated in vacuo. The residue was chromatographed over silica gel (25 g), eluting with a gradient of 1-3% methanol/chloroform. Appropriate fractions were combined and concentrated in vacuo to furnish 0.426 g (98%) of the title compound as an off-white solid. An analytical sample was prepared by recrystallization of this material from 3:1 ethyl acetate/hexane to give a white solid with mp 111°-112.5° C. and MS(EI) 321 (M+).

Workup

  1. temperaturethe reaction heated for a further 1.5 h, at which time TLC
  2. customthe reaction
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed over silica gel (25 g)
  6. washeluting with a gradient of 1-3% methanol/chloroform
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fabb0ce1d8c441d9d37cef8507da857
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

Loading…