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Sodium Azide → (5R)-5-(Azidomethyl)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one

HRID 1452571
Notes
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Reaction equation

HRID 1452571 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19]S(C)(=O)=O)[O:16][C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([CH2:19][C@@H:17]1[O:16][C:15](=[O:24])[N:14]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:18]1)=[N+:26]=[N-:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 68879798(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-[methanesulfonylmethyl]oxazolidin 2-one2×

Product 1

HCID 57526997(5R)-5-(Azidomethyl)-3-[3-Fluoro-4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-oneYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

(5R)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-[(methanesulfonyl)methyl]-oxazolidin 2-one (Intermediate 18) (5.0 g, 13.5 mmol) was dissolved in DMF (45 ml). Sodium azide (1.75 g, 27.0 mmol) was added and the reaction mixture was stirred at 70° C. for one hour. It was partitioned between ethyl acetate and saturated sodium bicarbonate, the organic phase was washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure to give the product as a white solid (4.1 g), which was used without further purification.

Workup

  1. customIt was partitioned between ethyl acetate and saturated sodium bicarbonate
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-639790482e9b4142a2207ec530bf8921
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07473699B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes