Lithium → HCID 54130332, compound

HRID 1602650Notes

Reaction equation

HRID 1602650 reaction equation
[Li].[C:2]([O:6][C:7](=[O:23])[NH:8][C@H:9]1[CH2:13][C@@H:12]([CH3:14])[N:11](CC2C=CC=CC=2)[C:10]1=[O:22])([CH3:5])([CH3:4])[CH3:3]>N.C1COCC1>[C:2]([O:6][C:7](=[O:23])[NH:8][C@H:9]1[CH2:13][C@@H:12]([CH3:14])[NH:11][C:10]1=[O:22])([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 2

HCID 3028194LithiumHCID 53688838HCID 53688838, compound

Product 1

HCID 54130332HCID 54130332, compound

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a blue solution of lithium metal (0.237 g, 34.2 mmol) in NH3 (1) (200 mL) at -78° C. was added a solution of 13-6 (2.60 g,8.54 mmol) in THF (15 mL). The mixture was stirred for 15 minutes, then quenched by the addition of ammonium chloride until the blue color dispersed. An additional 30 mL of THF was added, and the mixture warmed to 35° C. to evaporate the ammonia. MgSO4 was added,the mixture was filtered through a celite pad. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH) to give 13-7 as a colorless oil

Workup

  1. customquenched by the addition of ammonium chloride until the blue color
  2. additiondispersed
  3. additionAn additional 30 mL of THF was added
  4. customto evaporate the ammonia
  5. filtrationwas filtered through a celite pad
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 70:20:10 chloroform/ethyl acetate/MeOH)

Sources & evidence

ORD record
ord-87c084388ed245b6b96f713604a62c1e
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

Loading…