Sodium Azide → HCID 86591976, compound

HRID 1372802Notes

Reaction equation

HRID 1372802 reaction equation
[OH:1][C@@H:2]1[C@@H:9]2[C@@:5]([C:12]([O:14][CH3:15])=[O:13])([O:6][C:7]([CH3:11])([CH3:10])[O:8]2)[O:4][C@@H:3]1[CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O.[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:16][C@@H:3]1[O:4][C@@:5]2([C:12]([O:14][CH3:15])=[O:13])[O:6][C:7]([CH3:11])([CH3:10])[O:8][CH:9]2[C@@H:2]1[OH:1])=[N+:29]=[N-:30]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86591977HCID 86591977, compound

Product 1

HCID 86591976HCID 86591976, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 17 (400 mg, 1.0 mmol) in DMF (2 mL) was added NaN3 (97 mg, 1.5 mmol). The reaction mixture was heated at 100° C. (oil bath) for 20 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc/H2O. The EtOAc layer was washed with H2O (2×20 mL), brine (1×20 mL) and dried over MgSO4. EtOAc was evaporated and the crude material was purified by silica gel chromatography using EtOAc/Hexane. Product 15 was obtained as a white solid (140 mg; yield 52%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc/H2O
  3. washThe EtOAc layer was washed with H2O (2×20 mL), brine (1×20 mL)
  4. dry with materialdried over MgSO4
  5. customEtOAc was evaporated
  6. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-34157cf368f049428f35713e3396f32a
Source dataset
uspto-grants-2007_01
Patent number
US07160535B2

Reaction notes

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