Ammonia → HCID 69735819, compound

HRID 1859848Notes

Reaction equation

HRID 1859848 reaction equation
[NH3:1].[Li].C([O:10][C:11]([C:13]1([NH2:32])[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH3:30])[C:14]1=[O:31])=O)C1C=CC=CC=1.[C:33](O)([CH3:36])(C)C>C1COCC1>[NH2:1][C@H:33]([C:11]([C:13]1([NH2:32])[CH2:19][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]2[CH:26]=[CH:27][CH:28]=[CH:29][C:16]=2[N:15]([CH3:30])[C:14]1=[O:31])=[O:10])[CH3:36]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6386tert-ButanolHCID 3028194LithiumHCID 69735323HCID 69735323, compound

Product 1

HCID 69735819HCID 69735819, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

To a flask containing 300 mL of freshly condensed liquid ammonia at −70° C. was added lithium metal (4.1 equiv.). The dark blue slurry was warmed to −45° C. and treated with a pre-cooled solution of 3-(benzyloxycarbonyl)-amino-2,3-dihydro-1-methyl-5-phenyl-1H-1-benzazepin-2-one (Example 4-AC, Steps A-C) in 30 mL distilled THF. After 10 min a solution of tert-butanol (4.0 equiv.) in distilled THF was added. After an additional 10 min the reaction was quenched with ammonium chloride. The cooling bath w as removed and the ammonia allowed to evaporate overnight. The contents were partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic phase was washed with brine, dried over Na2SO4, filtered, and concentrated. Purified via liquid chromatography eluting with a gradient from 99:1 to 90:10 CH2Cl2/MeOH.

Workup

  1. additionTo a flask containing
  2. distillationdistilled THF
  3. customAfter an additional 10 min the reaction was quenched with ammonium chloride
  4. customThe cooling bath w as removed
  5. customto evaporate overnight
  6. customThe contents were partitioned between CH2Cl2 and saturated aqueous NaHCO3
  7. washThe organic phase was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurified via liquid chromatography
  12. washeluting with a gradient from 99:1 to 90:10 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-bfaa1f518a444f89b29b5450700e98a0
Source dataset
uspto-grants-2003_03
Patent number
US06528505B1

Reaction notes

Loading…