Sodium Azide → HCID 14842617, compound

HRID 1786551Notes

Reaction equation

HRID 1786551 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][N:7]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:5].[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([N:29]=[N+:30]=[N-:31])[CH2:8][N:7]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:5]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57114913HCID 57114913, compound

Product 1

HCID 14842617HCID 14842617, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of (2S,4R)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester) (28) (2.6 g, 6.3 mmol) in dry DMF (15 ml) was added NaN3 (0.41 g, 6.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate: water (10:1) (150 ml). The organic layer was washed with water (30 ml, 2×), dried over MgSO4 and evaporated to dryness The resulting residue was purified by column chromatography using pet ether: CH2Cl2: MeOH (10:1) to give 1.8 g of desired product.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic layer was washed with water (30 ml, 2×)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness The resulting residue
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8f69ce2be3a64ab4ba0c5693a2c95f75
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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