Ammonia → HCID 71313226, compound

HRID 2105888Notes

Reaction equation

HRID 2105888 reaction equation
[CH3:1][C@@H:2]1[CH2:24][C:23]2[C:25](=[O:26])[C:18](=[CH:19][C:20]([C:22]=2OC)=[O:21])[NH:17][C:15](=[O:16])[C:14]([CH3:29])=[CH:13][CH:12]=[CH:11][C@H:10]([O:30][CH3:31])[C@@H:9]([O:32][C:33]([NH2:35])=[O:34])[C:8]([CH3:36])=[CH:7][C@H:6]([CH3:37])[C@@H:5]([OH:38])[C@@H:4]([O:39][CH3:40])[CH2:3]1.[NH3:41]>C1COCC1>[CH3:1][C@@H:2]1[CH2:24][C:23]2[C:25](=[O:26])[C:18](=[CH:19][C:20]([C:22]=2[NH2:41])=[O:21])[NH:17][C:15](=[O:16])[C:14]([CH3:29])=[CH:13][CH:12]=[CH:11][C@@H:10]([O:30][CH3:31])[C@@H:9]([O:32][C:33]([NH2:35])=[O:34])[C:8]([CH3:36])=[CH:7][C@H:6]([CH3:37])[C@@H:5]([OH:38])[C@H:4]([O:39][CH3:40])[CH2:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5288382Geldanamycin

Product 1

HCID 71313226HCID 71313226, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.0 g (3.57 mmol) of geldanamycin in 40 ml of dry THF in a flame-dried flask was added 2.55 ml (17.8 mmol, solution in methanol, ca 7N) of ammonia under nitrogen. The reaction mixture was stirred at room temperature for 24 h at which time TLC analysis indicated the reaction was complete. The solvent was removed by rotary evaporation and the crude material was dissolved in 30 mL of EtOH and crystallized by addition of 120 mL of water to give 1.8 g (3.30 mmol) of 17-AG as red crystals (99% pure by HPLC). MP 284-286° C. 1H NMR and HPLC are consistent with the desired product.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe crude material was dissolved in 30 mL of EtOH
  3. customcrystallized by addition of 120 mL of water

Sources & evidence

ORD record
ord-24d15619185a412ca7e038ca3650263f
Source dataset
uspto-grants-2009_08
Patent number
US07579462B2

Reaction notes

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