Stannous chloride dihydrate → HCID 21103285, compound

HRID 1354085Notes

Reaction equation

HRID 1354085 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][C:17](=[O:19])[N:16]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH:14]2[C:28]([O:30][CH3:31])=[O:29])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+].CO[CH:44]1[CH2:48][CH2:47][CH:46](OC)O1>CO.C(OCC)(=O)C.C(O)(=O)C>[CH2:20]([N:16]1[C:17](=[O:19])[CH2:18][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([N:1]3[CH:44]=[CH:48][CH:47]=[CH:46]3)=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH:14]([C:28]([O:30][CH3:31])=[O:29])[CH2:15]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 790982,5-DimethoxytetrahydrofuranHCID 516892Sodium BicarbonateHCID 21103276HCID 21103276, compound

Product 1

HCID 21103285HCID 21103285, compoundYield 26.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

The compound of Example 56 (0.69 g, 1.5 mmol) was put in 10 mL of a MeOH solution to which SnCl2.2H2O (1.37 g, 6.4 mmol) was added, and stirred for 1.5 hours while maintaining the temperature at 50° C. A saturated NaHCO3 aqueous solution was introduced and stirred for 2 hours, and then it was extracted with ethyl acetate. After distillation under reduced pressure, 2,5-dimethoxytetrahydrofuran (0.20 mLo, 1.5 mmol) and 1 mL of acetic acid were introduced and refluxed for 2 hours. 50 mL of ethyl acetate was introduced and the reactant was washed with 50 mL of a saturated NaHCO3 aqueous solution and 50 mL of a 1 N HCl aqueous solution, and dried and then concentrated under reduced pressure. The mixture was separated with hexane and ethyl acetate (3:1) in a silica gel column to obtain a yellow oily title compound (0.19 g, 26%).

Workup

  1. additionwas added
  2. stirringstirred for 2 hours
  3. extractionit was extracted with ethyl acetate
  4. additionwere introduced
  5. temperaturerefluxed for 2 hours
  6. washthe reactant was washed with 50 mL of a saturated NaHCO3 aqueous solution and 50 mL of a 1 N HCl aqueous solution
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe mixture was separated with hexane and ethyl acetate (3:1) in a silica gel column

Sources & evidence

ORD record
ord-a46191c28c3f4db2a3033f22bb2ddde4
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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