Sodium Thiosulfate → HCID 60073847, compound

HRID 1061687Notes

Reaction equation

HRID 1061687 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([N:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]([CH2:38][C:39]([NH:41][C@@H:42]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:43]([C:45]2[O:46][CH2:47][C:48]([CH3:51])([CH3:50])[N:49]=2)[OH:44])=[O:40])[C:28](=[O:59])[CH:27]1[CH:60]([CH3:62])[CH3:61])(=[O:25])[CH3:24].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(O)(C)(C)C>[C:23]([N:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]([CH2:38][C:39]([NH:41][C@@H:42]([CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:43]([C:45]2[O:46][CH2:47][C:48]([CH3:51])([CH3:50])[N:49]=2)=[O:44])=[O:40])[C:28](=[O:59])[CH:27]1[CH:60]([CH3:62])[CH3:61])(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 60073830HCID 60073830, compound

Product 1

HCID 60073847HCID 60073847, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Dess-Martin oxidizing reagent (293 mg) and tert-butanol (650 μl) are added to a solution of (1RS,2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-1-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-3-phenyl-1-propanol (93.3 mg, Compound No. 9-1) in methylene chloride (2.5 ml), and the mixture is stirred for one day. A saturated aqueous sodium hydrogencarbonate solution (6 ml) and an aqueous sodium thiosulfate solution (6 ml) are added to the reaction mixture, and the whole is stirred and then extracted with ethyl acetate. The extract is washed with an aqueous sodium thiosulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (43.8 mg).

Workup

  1. stirringthe whole is stirred
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with an aqueous sodium thiosulfate solution
  4. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine successively and dried over anhydrous magnesium sulfate
  5. concentrationThe extract is concentrated under reduced pressure
  6. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-38cae6d32461494da613e6c2b0b51594
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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