61350-60-5 → HCID 68961477, compound

HRID 1431940Notes

Reaction equation

HRID 1431940 reaction equation
[Si]([C:5]1[N:6]=NN[CH:9]=1)(C)(C)C.[N:10]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12](Cl)=[O:13]>S1(CCCC1)(=O)=O.[Cl-].[Na+].O>[CH2:21]([O:20][C:18]([N:10]1[CH2:17][CH2:16][CH2:15][CH:11]1[C:12]1[O:13][CH:9]=[CH:5][N:6]=1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 1103285461350-60-5HCID 178504166HCID 178504166, compound

Product 1

HCID 68961477HCID 68961477, compound

Reagents, catalysts & solvents 2

HCID 31347SulfolaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of TMS-triazole (14.17 g, 100.3 mmol, 1 equiv.) in sulfolane (290 mL) at rt under nitrogen, is added dropwise Z-L-Pro-Cl (26.85 g, 100.3 mmol, 1 equiv.) in sulfolane (70 mL). The resulting mixture is stirred at rt for 30 minutes, then the temperature is elevated to 140° C. for 3 hours. After the reaction mixture is cooled to rt, poured into excess brine and extracted with diethyl ether. The diethyl ether extracts are washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. The residue is purified by flash chromatography (DCM:acetone=9:1) to give the title compound as a light yellow oil.

Workup

  1. waitthe temperature is elevated to 140° C. for 3 hours
  2. temperatureAfter the reaction mixture is cooled to rt
  3. extractionextracted with diethyl ether
  4. washThe diethyl ether extracts are washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by flash chromatography (DCM:acetone=9:1)

Sources & evidence

ORD record
ord-17fe2430fca64e4ab50084c8d37b167a
Source dataset
uspto-grants-2009_11
Patent number
US07612059B2

Reaction notes

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