Sodium Azide → HCID 86590231, compound

HRID 723751Notes

Reaction equation

HRID 723751 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22]OS(C)(=O)=O)[O:19][C:18]4=[O:28])=[CH:13][C:12]=3[F:29])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O.O>[O:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][N:30]=[N+:31]=[N-:32])[O:19][C:18]4=[O:28])=[CH:13][C:12]=3[F:29])[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 60133546HCID 60133546, compound

Product 1

HCID 86590231HCID 86590231, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-(4-(1,4-Dioxa-8-azaspiro[4,5]dec-8-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyl-oxazolidin-2-one (3.03 g, 7.04 mM) was dissolved in N,N-dimethylformamide (50 ml), treated with sodium azide (732 mg, 11.3 mM), and heated with stirring at 50° for 4 hours. After cooling the mixture was diluted with water (250 ml), and extracted into ethyl acetate (3×100 ml). The combined organics were dried (magnesium sulfate), and evaporated to give product (2.44 g), of sufficient quality for use without purification.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture
  3. extractionextracted into ethyl acetate (3×100 ml)
  4. dry with materialThe combined organics were dried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-b5ee9a47b5f04f178a39baf24d87c59d
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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