Stannous chloride dihydrate → HCID 10126248, compound

HRID 1059851Notes

Reaction equation

HRID 1059851 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-ae7d7af60e3842e19b00f15b5f231624
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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