Stannous chloride dihydrate → HCID 10126248, compound

HRID 583940Notes

Reaction equation

HRID 583940 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([S:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-])=O)[CH:14]=2)(=[O:11])=[O:10])[CH:6]=[C:5]([O:24][CH3:25])[C:4]=1[O:26][CH3:27].O.O.Cl[Sn]Cl>CO>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][S:9]([C:7]2[CH:6]=[C:5]([O:24][CH3:25])[C:4]([O:26][CH3:27])=[C:3]([O:2][CH3:1])[CH:8]=2)(=[O:11])=[O:10])=[CH:14][C:15]=1[NH2:21]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22344724HCID 22344724, compound

Product 1

HCID 10126248HCID 10126248, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 91A (490 mg, 1.23 mmol) in methanol (10 mL) was treated with SnCl2.2H2O (1.39 g; 6.17 mmol), heated to reflux for 1 hour, and concentrated. The concentrate was partitioned between saturated NaHCO3 and ethyl acetate, and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/dichloromethane to provide the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated
  4. customThe concentrate was partitioned between saturated NaHCO3 and ethyl acetate
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by flash column chromatography on silica gel with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-fce0627078294a35b4d76fd5b52ea021
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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