Ammonia → HCID 18394796, compound

HRID 1602635Notes

Reaction equation

HRID 1602635 reaction equation
N.[Li].C([N:10]1[C@H:14]([CH3:15])[CH2:13][C@H:12]([CH2:16][CH2:17][C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[C:11]1=[O:24])C1C=CC=CC=1>CO.C1COCC1>[CH3:15][C@H:14]1[NH:10][C:11](=[O:24])[C@@H:12]([CH2:16][CH2:17][C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH2:13]1

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 3028194LithiumHCID 18394777HCID 18394777, compound

Product 1

HCID 18394796HCID 18394796, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 3-necked 500 mL flask at -78° C. was condensed 200 mL of ammonia. Lithium (64 mg, 9.25 mmol) was washed with MeOH, then THF and then added to the ammonia. After 20 minutes, 11-6 (560 mg, 1.85 mmol), dissolved in 25 mL of THF, was added. After 30 minutes, the reaction was quenched with NH4Cl; 200 mL of THF was added, the cooling bath was removed and the solution purged with argon for 30 minutes to remove the ammonia. The solution was dried (MgSO4) and concentrated. Flash chromatography (silica, EtOAc→5% MeOH/EtOAc) gave 11-7 as an oil.

Workup

  1. customInto a 3-necked 500 mL flask at -78° C. was
  2. additionwas added
  3. waitAfter 30 minutes
  4. customthe reaction was quenched with NH4Cl
  5. addition200 mL of THF was added
  6. customthe cooling bath was removed
  7. customthe solution purged with argon for 30 minutes
  8. customto remove the ammonia
  9. dry with materialThe solution was dried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-ea7ad70a59694c5fa255c87373fde3c3
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

Loading…