Sodium Azide → HCID 53844923, compound

HRID 1108596Notes

Reaction equation

HRID 1108596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@H:21]([CH2:23]OS(C)(=O)=O)[O:20][C:19]2=[O:29])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][F:16])[C:10](=[O:17])[CH2:9]1.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[N:30]([CH2:23][C@@H:21]1[O:20][C:19](=[O:29])[N:18]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][F:16])[C:10](=[O:17])[CH2:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:22]1)=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53883525HCID 53883525, compound

Product 1

HCID 53844923HCID 53844923, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(5R)-3-(3-Fluoro-4-{4-(2-fluoroethyl)-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyl-oxymethyl)oxazolidin-2-one (719 mg) was dissolved in dry DMF (15 ml), and sodium azide (647 mg) added to the mixture. The mixture was heated at 80° C. for 6 hours, and then evaporated to dryness. The resulting residue was dissolved in ethyl acetate, washed twice with water, and dried (MgSO4). Evaporation gave (5R)-5-azidomethyl-3-(3-fluoro-4-(4-(2-fluoroethyl)-3-oxopiperazin-1-yl)phenyl)oxazolidin-2-one (413 mg) which was used without further purification.

Workup

  1. customevaporated to dryness
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialdried (MgSO4)
  5. customEvaporation

Sources & evidence

ORD record
ord-b2741a2341ea46d0b9312a2e82c0ff28
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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