Sodium Azide → HCID 86761239, compound

HRID 2265239Notes

Reaction equation

HRID 2265239 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4](OS(C)(=O)=O)[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:6].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([N:21]=[N+:22]=[N-:23])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86761237HCID 86761237, compound

Product 1

HCID 86761239HCID 86761239, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (2R,3R)-3-(3,4-dichloro-phenyl)-2-methanesulfonyloxy-butyric acid methyl ester (0.70 g, 2.05 mmol) in DMF (10 mL) was added NaN3 (0.27 g, 4.10 mmol). The reaction was heated at 55° C. overnight. The mixture was quenched with water and extracted with EtOAc. The organic phase was washed with water (2×), dried (MgSO4), and concentrated. The product was purified by flash chromatography to give 0.42 g (71%) of product. 1H NMR (500 MHz, CDCl3): 7.39 (d, J=8.3, 1H), 7.35 (d, J=2.1, 1H), 7.10 (dd, J=8.3, 2.1, 1H), 3.96 (d, J=6.4, 1H), 3.71 (s, 3H), 3.29 (m, 1H), 1.33 (d, J=7.0, 3H).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water (2×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-fcfed6cd473749a49aa8070fbb28279b
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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