Hydrochloric Acid → 17-n-Propylamino-geldanamycin

HRID 443796Notes

Reaction equation

HRID 443796 reaction equation
C(Cl)(Cl)Cl.[CH3:5][C@@H:6]1[CH2:28][C:27]2[C:29](=[O:30])[C:22](=[CH:23][C:24]([C:26]=2OC)=[O:25])[NH:21][C:19](=[O:20])[C:18]([CH3:33])=[CH:17][CH:16]=[CH:15][C@H:14]([O:34][CH3:35])[C@@H:13]([O:36][C:37]([NH2:39])=[O:38])[C:12]([CH3:40])=[CH:11][C@H:10]([CH3:41])[C@@H:9]([OH:42])[C@@H:8]([O:43][CH3:44])[CH2:7]1.[CH2:45]([NH2:48])[CH2:46][CH3:47].Cl>O>[CH3:47][CH2:46][CH2:45][NH:48][C:26]1[C:24](=[O:25])[CH:23]=[C:22]2[C:29](=[O:30])[C:27]=1[CH2:28][CH:6]([CH3:5])[CH2:7][CH:8]([O:43][CH3:44])[C@@H:9]([OH:42])[C@H:10]([CH3:41])[CH:11]=[C:12]([CH3:40])[CH:13]([O:36][C:37]([NH2:39])=[O:38])[CH:14]([O:34][CH3:35])[CH:15]=[CH:16][CH:17]=[C:18]([CH3:33])[C:19]([NH:21]2)=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 7852PropylamineHCID 5288382Geldanamycin

Product 1

HCID 547288417-n-Propylamino-geldanamycinYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 50 ml. of chloroform, 280 mg. of Geldanamycin was dissolved and then, 1 ml. of n-propylamine was added. The mixture was stirred at room temperature for 1 hour and the mixture was charged into 50 ml. of cold water and then, pH was adjusted 3 with 6 N-HCl. The chloroform layer was separated and the water layer was extructed with 50 ml. of chloroform. Both chloroform layers were combined and dehydrated over anhydrous sodium sulfate for 2 hours. Chloroform was distilled off under a reduced pressure to remain a reddish violet solid product. The solid product was recrystallized from acetone-n-hexane to obtain 286 mg. (yield 98%) of 17-n-propylamino-Geldanamycin as reddish violet acicular crystal.

Workup

  1. additionthe mixture was charged into 50 ml
  2. customThe chloroform layer was separated
  3. waitdehydrated over anhydrous sodium sulfate for 2 hours
  4. distillationChloroform was distilled off under a reduced pressure
  5. customThe solid product was recrystallized from acetone-n-hexane
  6. customto obtain 286 mg

Sources & evidence

ORD record
ord-2a91ab5206854ce1ab59095fb1054b7e
Source dataset
uspto-grants-1981_04
Patent number
US04261989

Reaction notes

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