Hydrochloric Acid → Retaspimycin hydrochloride

HRID 1674503Notes

Reaction equation

HRID 1674503 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]=2[NH:27][CH2:28][CH:29]=[CH2:30])=[O:21])[NH:17][C:15](=[O:16])[C:14]([CH3:31])=[CH:13][CH:12]=[CH:11][C@H:10]([O:32][CH3:33])[C@@H:9]([O:34][C:35]([NH2:37])=[O:36])[C:8]([CH3:38])=[CH:7][C@H:6]([CH3:39])[C@@H:5]([OH:40])[C@@H:4]([O:41][CH3:42])[CH2:3]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[ClH:51].O1CCOCC1>ClCCl>[CH3:1][C@H:2]1[CH2:3][C@H:4]([O:41][CH3:42])[C@H:5]([OH:40])[C@@H:6]([CH3:39])[CH:7]=[C:8]([CH3:38])[C@H:9]([O:34][C:35]([NH2:37])=[O:36])[C@@H:10]([O:32][CH3:33])[CH:11]=[CH:12][CH:13]=[C:14]([CH3:31])[C:15](=[O:16])[NH:17][C:18]2=[C:25]([OH:26])[C:23](=[C:22]([NH:27][CH2:28][CH:29]=[CH2:30])[C:20]([OH:21])=[CH:19]2)[CH2:24]1.[ClH:51]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 6505803Tanespimycin

Product 1

HCID 11685945Retaspimycin hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound of Formula (1) (0.450 g, 0.768 mmol, 1.0 equiv) is dissolved in dichloromethane (50 mL) and stirred with a 10% aqueous solution of sodium hydrosulfite (50 mL). The solution is stirred for 30 minutes. The organic layer was collected, dried over Na2SO4, filtered and transferred to a round bottom flask. To this solution was added a solution of HCl in dioxane (4 N, 0.211 mL, 1.1 equiv.). The resulting mixture was allowed to stir under nitrogen for 30 minutes. A yellow solid slowly crashed out of solution. The yellow solid was purified by recrystallization form MeOH/EtOAc to yield 0.386 g of the IPI-504 (15).

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customtransferred to a round bottom flask
  5. stirringto stir under nitrogen for 30 minutes
  6. customThe yellow solid was purified by recrystallization
  7. customform MeOH/EtOAc

Sources & evidence

ORD record
ord-59be53d0e24a49be9740d792ca4bd392
Source dataset
uspto-grants-2011_08
Patent number
US08003634B2

Reaction notes

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