Water → HCID 10314617, compound

HRID 583558Notes

Reaction equation

HRID 583558 reaction equation
I[CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([F:22])[CH:10]=2)[CH2:4]1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C=O)C>[N:23]([CH2:2][CH:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([F:22])[CH:10]=2)[CH2:4]1)=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 10476981HCID 10476981, compound

Product 1

HCID 10314617HCID 10314617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-5-(Iodomethyl)-3-[4-(3-pyridyl)-3,5-difluorophenyl]-2-oxazolidinone (PREPARATION 5, 577 mg, 1.31 mmol) in DMF (dried over 4A sieves, 15 ml) is combined with sodium azide (681 mg, 10.5 mmol, 8 eq). The reaction is placed under an atmosphere of nitrogen and heated to 55°. After 2 hr, the reaction is added to water (100 ml) and then extracted with ethyl acetate (4×25 ml). The combined organic extracts are combined and are washed with water then brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The crude azide is suitable for reduction without further purification. An analytical sample is prepared by preparative TLC (silica gel) eluting with acetonitrile/chloroform (10/90). The appropriate fractions are pooled and concentrated to give the title compound, mp 97-98°; FTIR (mull) cm-1 3483, 2110, 1746, 1640, 1417, 1237, 1064 and 716; MS (EI, m/z) 331, 274, 258, 232, 217, 190 and 43; NMR (CDCl3) 8.72, 8.63, 7.79, 7.42-7.38, 7.34, 4.90-4.82, 4.11, 3.88, 3.77 and 3.63 δ.

Workup

  1. temperatureheated to 55°
  2. extractionextracted with ethyl acetate (4×25 ml)
  3. washare washed with water
  4. dry with materialbrine, dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude azide is suitable for reduction without further purification
  8. customAn analytical sample is prepared by preparative TLC (silica gel)
  9. washeluting with acetonitrile/chloroform (10/90)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0ffc463585ad48a7b04ee3549bcd73f3
Source dataset
uspto-grants-1999_07
Patent number
US05929248

Reaction notes

Loading…