Ammonia → Ipi-493

HRID 1622214Notes

Reaction equation

HRID 1622214 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]>CO.ClCCl>[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

5

Reactant 2

HCID 222AmmoniaHCID 5288382Geldanamycin

Product 1

HCID 9893658Ipi-493

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Geldanamycin (1.12 g, 2 mmol, 1 eq) was added to anhydrous dichloromethane (5 mL). NH3 in methanol was added to this solution (9 mL, 100 mmol, 50 eq) and was allowed to stir for 24 hours. The reaction solution was diluted with dichloromethane and extracted with water, followed by dilute HCl. The organic layer was collected washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield a purple solid. This solid was recrystalized twice from acetone/heptanes to yield 0.239 of 17-amino-17-demethoxygeldanamycin (17-AG).

Workup

  1. extractionextracted with water
  2. customThe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto yield a purple solid
  7. customThis solid was recrystalized twice from acetone/heptanes

Sources & evidence

ORD record
ord-c5120e90b6454208808dbb80150f6022
Source dataset
uspto-grants-2014_07
Patent number
US08778921B2

Reaction notes

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