Water → HCID 11771306, compound

HRID 582534Notes

Reaction equation

HRID 582534 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:25])[NH:10][C@H:11]([CH2:19]OS(C)(=O)=O)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:26]=[N+:27]=[N-:28].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9](=[O:25])[NH:10][C@H:11]([CH2:19][N:26]=[N+:27]=[N-:28])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 54080588HCID 54080588, compound

Product 1

HCID 11771306HCID 11771306, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-[1-[[(methylsulphonyl)oxy]methyl]-2-phenylethyl]carbamic acid phenylmethyl ester (2.0 g,5.5 mmol) in dimethylformamide (35 ml) was heated with sodium azide (0.43 g,6.6 mmol) at 80° C. for 4.5h. The reaction was then cooled and poured into iced water (100 ml) and ethyl acetate (70 ml). The aqueous phase was extracted with ethyl acetate (2×70 ml) and the combined extract was washed with water (50 ml), dried (MgSO4) and evaporated to leave an oil which was purified by flash chromatography eluting with 20% ethyl acetate in cyclohexane to give the title compound (1.51 g) as an oil, MH+ =312.

Workup

  1. temperatureThe reaction was then cooled
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×70 ml)
  3. extractionthe combined extract
  4. washwas washed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto leave an oil which
  8. customwas purified by flash chromatography
  9. washeluting with 20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-1433e177d8c14fb1988aa9b4c4e9a783
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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