Tributyltin Chloride → HCID 69287612, compound

HRID 2222440Notes

Reaction equation

HRID 2222440 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16](OC(SC)=S)[C:17]2([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][O:18]2)[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](Cl)(CCCC)CCCC)CCC.[F-].[K+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][C:17]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][CH2:19][O:18]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 522689Potassium FluorideHCID 86596095HCID 86596095, compound

Product 1

HCID 69287612HCID 69287612, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 2-((3-{[(t-butoxycarbonyl)-amino]methyl}phenyl){[(methylsulfanyl)carbothioyl]oxy}-methyl)tetrahydro-2-furancarboxylate in 30 ml of toluene were added 1.55 g of tri-n-butyltin chloride and 0.03 g of 2,2-diazobis(isobutyronitrile) under an atmosphere of nitrogen gas, and the mixture was heated under reflux for 23 hours. After cooling to room temperature, 100 ml of saturated aqueous potassium fluoride was added. After stirring for 30 minutes, the mixture was extracted with 200 ml of ethyl acetate. The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 1.26 g of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 23 hours
  3. extractionthe mixture was extracted with 200 ml of ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1bc94769d4c14dacaa50d0cf0322c4bd
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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