Ethanol → HCID 57523007, compound

HRID 1746347Notes

Reaction equation

HRID 1746347 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[C@H:11]2[C@H:9]([O:10]2)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:6]1.[NH4+].[Cl-].[N-:18]=[N+:19]=[N-:20].[Na+].CCO>CN(C=O)C.CCO.O>[N:18]([C@@H:9]1[C@@H:11]([OH:10])[C@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6][C:7]([C:12]([O:14][CH3:15])=[O:13])=[CH:8]1)=[N+:19]=[N-:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57523006HCID 57523006, compound

Product 1

HCID 57523007HCID 57523007, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 86633292ethanol water DMFSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of cyclic epoxy ester 14 (107 mg, 0.5 mmol) in DMF/EtOH/H2O (1:1:0.5 mL) were added NH4Cl (160.5 g, 3 mmol) and NaN3 (197.4 g, 3 mmol) at 0° C. The mixture was then stirred at 25° C. for 10 h. After completion of reaction (monitored by TLC), EtOH was removed by rotary evaporation. The remaining solution was extracted with EtOAc (100 mL×3). The combined organic layers were washed with, brine (20 mL×6) and dried (Na2SO4). After evaporation of the solvent, the residue was purified by chromatography (petroleum ether/ethyl acetate (7/3 v/v) to obtain compound 15.

Workup

  1. customwas removed by rotary evaporation
  2. extractionThe remaining solution was extracted with EtOAc (100 mL×3)
  3. washThe combined organic layers were washed with, brine (20 mL×6)
  4. dry with materialdried (Na2SO4)
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by chromatography (petroleum ether/ethyl acetate (7/3 v/v)

Sources & evidence

ORD record
ord-a6b46ddd2174477d95a20991a3378880
Source dataset
uspto-grants-2015_10
Patent number
US09150498B2

Reaction notes

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