Ammonia → HCID 18394801, compound

HRID 322519Notes

Reaction equation

HRID 322519 reaction equation
N.C([N:9]1[C@H:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][C@H:11]([CH2:21][CH2:22][C:23]2([CH3:28])[O:27][CH2:26][CH2:25][O:24]2)[C:10]1=[O:29])C1C=CC=CC=1.[Li]>C1COCC1.CO>[CH2:14]([C@H:13]1[NH:9][C:10](=[O:29])[C@@H:11]([CH2:21][CH2:22][C:23]2([CH3:28])[O:27][CH2:26][CH2:25][O:24]2)[CH2:12]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 3028194LithiumHCID 18394779HCID 18394779, compound

Product 1

HCID 18394801HCID 18394801, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 3-necked 500 mL flask at −78° C. was condensed 100 mL of ammonia. Next, 12-2 (470 mg, 1.24 mmol), dissolved in 20 mL of THF, was added. Lithium (19 mg, 2.48 mmol) was washed with MeOH, then THF and then added to the ammonia. After 20 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) gave 12-3 as an oil.

Workup

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

Sources & evidence

ORD record
ord-990e8e63e7774f629d16da44ff58e1c4
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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