Sodium Azide → HCID 86590232, compound

HRID 723758Notes

Reaction equation

HRID 723758 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25]OS(C)(=O)=O)[O:22][C:21]3=[O:31])=[CH:16][C:15]=2[F:32])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][N:33]=[N+:34]=[N-:35])[O:22][C:21]3=[O:31])=[CH:16][C:15]=2[F:32])[CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86590233HCID 86590233, compound

Product 1

HCID 86590232HCID 86590232, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-(4-((3R)-3-(t-butoxycarbonyl)aminopyrrolidin-1-yl)-3-fluorophenyl)-5-methane-sulfonyloxymethyloxazolidin-2-one (1.25 g, 2.64 mM) was dissolved in N,N-dimethyl-formamide (20 ml), treated with sodium azide (275 mg, 4.23 mM), and heated with stirring at 50° for 5 hours. After cooling the mixture was diluted with water (100 ml), and extracted into ethyl acetate (3×75 ml). The combined organics were dried (magnesium sulfate), and evaporated to give a yellow solid, which 5:19 PM was recrystallised from isopropanol to give the required product (715 mg).

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture
  3. extractionextracted into ethyl acetate (3×75 ml)
  4. dry with materialThe combined organics were dried (magnesium sulfate)
  5. customevaporated
  6. customto give a yellow solid, which 5:19 PM
  7. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-53ba5ef1c8584369ba8364e7965ed4fd
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

Loading…