Sodium Azide → HCID 86632371, compound

HRID 2428157Notes

Reaction equation

HRID 2428157 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([N:12]([CH2:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:20]=[CH:21][C:22]=1[Cl:23])[CH:13]1[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10](=[O:11])[N:12]([CH2:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][N:1]=[N+:2]=[N-:3])[CH:20]=[CH:21][C:22]=1[Cl:23])[CH:13]1[CH2:15][CH2:14]1)([CH3:7])([CH3:6])[CH3:8]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86632370HCID 86632370, compound

Product 1

HCID 86632371HCID 86632371, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

NaN3 (1.17 g, 18.0 mmol) was added to a sol. of toluene-4-sulfonic acid 2-{3-[(tert-butoxycarbonyl-cyclopropyl-amino)-methyl]-4-chloro-phenyl}-ethyl ester (2.16 g, 4.50 mmol) in DMF (45 mL). The mixture was heated to 65° C., and stirred at this temperature for 1.5 h. The mixture was allowed to cool to rt, and poured onto water. The mixture was extracted with TBME (3×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 95:5) yielded the title compound (1.49 g, 94%). LC-MS: tR=1.11 min; ES+: 336.43.

Workup

  1. temperatureto cool to rt
  2. additionpoured onto water
  3. extractionThe mixture was extracted with TBME (3×)
  4. washextracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the crude by FC (heptane/EtOAc 95:5)

Sources & evidence

ORD record
ord-2ee05740c9f2409190fe84a745524d56
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…