Hydrochloric Acid → HCID 60077638, compound

HRID 2084467Notes

Reaction equation

HRID 2084467 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21](C(NN)=O)[N:20]=2)[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[N:29]([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CC(O)=O>[NH2:29][C:21]1[N:20]=[C:19]([C@H:10]([CH2:9][CH2:8][CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:11][C:12]([OH:14])=[O:13])[O:23][N:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 60077680HCID 60077680, compound

Product 1

HCID 60077638HCID 60077638, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-[3-(hydrazinocarbonyl)-1,2,4-oxadiazol-5-yl]hexanoate (preparation 71) (1.06 g, 2.76 mmol) in glacial AcOH (10 ml) was treated with 2M HCl (10 ml) and stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0° C. before being treated with a solution of NaNO2 (278 mg, in 5 ml H2O) making sure the temperature never rose above 5° C. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to room temperature before being heated at 85° C. until the evolution of gas a finished. The reaction mixture was neutralised with sat. Na2CO3 solution and extracted with EtOAc. The organic extract was washed with brine and the solvent removed under reduced pressure. The residue was treated with TFA (4 ml) and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue azeotroped from toluene (×3) and DCM (×3) to afford the title compound as a foam (390 mg, 50%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe temperature never rose above 5° C
  3. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  4. temperatureto warm to room temperature
  5. temperaturebefore being heated at 85° C. until the evolution of gas
  6. extractionextracted with EtOAc
  7. extractionThe organic extract
  8. washwas washed with brine
  9. customthe solvent removed under reduced pressure
  10. additionThe residue was treated with TFA (4 ml)
  11. stirringstirred at room temperature for 1 hour
  12. customThe solvent was removed under reduced pressure
  13. customthe residue azeotroped from toluene (×3) and DCM (×3)

Sources & evidence

ORD record
ord-74cf2864d43c46428f4961871b4cca02
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

Loading…