Dibutyltin oxide → HCID 178520423, compound

HRID 1953528Notes

Reaction equation

HRID 1953528 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)=[CH:4][C:3]=2[O:2]1.C[Si]([N:39]=[N+:40]=[N-:41])(C)C.C([Sn](=O)CCCC)CCC.C(Cl)Cl.CO>C1(C)C=CC=CC=1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]3[CH:27]=[CH:28][C:29]([C:32]4[NH:41][N:40]=[N:39][N:33]=4)=[CH:30][CH:31]=3)=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 15887799HCID 15887799, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 178520423HCID 178520423, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of Example 32 (0.25 g, 0.56 mmol) in 10 mL of toluene were added successively trimethylsilylazide (0.30 mL, 4 equiv.) and dibutyltinoxide (0.06 g, 0.4 equiv.). The resulting mixture was stirred at reflux for two days. Tlc monitoring showed formation of a new compound (DCM:MeOH (80:20), Rf=0.35). The reaction mixture was concentrated in vacuo. The resulting yellow gum was dissolved in MeOH and concentrated in vacuo. The residue was partitioned between EtOAc (25 mL) and an aqueous saturated solution of NaHCO3 (25 mL). The organic phase was extracted with an additional portion of an aqueous saturated solution of NaHCO3 (25 mL). The combined aqueous extracts were acidified to pH=2 with HCl (1N) and then extracted with EtOAc (2×25 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to give a yellow powder that was purified via flash chromatography (SiO2, DCM:MeOH (90:10)). Recrystallization from 2-propanol:iPr2O (1:1) gave the title compound (0.19 g, 70%) as white crystals.

Workup

  1. temperatureat reflux for two days
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe resulting yellow gum was dissolved in MeOH
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between EtOAc (25 mL)
  6. extractionThe organic phase was extracted with an additional portion of an aqueous saturated solution of NaHCO3 (25 mL)
  7. extractionextracted with EtOAc (2×25 mL)
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow powder that
  12. customwas purified via flash chromatography (SiO2, DCM:MeOH (90:10))
  13. customRecrystallization from 2-propanol:iPr2O (1:1)

Sources & evidence

ORD record
ord-2b79d33dab0c423d884a5c996fe496f3
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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