Sodium Bicarbonate → HCID 68972825, compound

HRID 600723Notes

Reaction equation

HRID 600723 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:13][N:14]=[C:15](Cl)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[C:4]([O:3][C:1]([N:8]1[CH2:12][C@H:11]2[C@H:10]([C:15]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:14][O:13]2)[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 53404818N-Hydroxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 68972825HCID 68972825, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-Boc pyrroline (270 mg; 1.60 mmol), chloro oxime 2f (470 mg; 3.00 mmol) and sodium bicarbonate (760 mg; 9.04 mmol) in isopropanol (10 mL) were heated at 40° C. overnight. An additional portion of chloro oxime and sodium bicarbonate was added and heating continued for 20 hours. After cooling, the volatiles were evaporated. The residue was dissolved in ethyl acetate (50 mL), and washed with water (50 mL). The organic layer was dried (MgSO4), filtered and evaporated. Cycloadduct 3f was isolated as a beige powder after chromatography with 70% ethyl acetate/hexanes.

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. customthe volatiles were evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with water (50 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b7f39c03002d454997fe65f62739fb76
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

Loading…