Tetrabutylammonium Fluoride → HCID 57789264, compound

HRID 1625549Notes

Reaction equation

HRID 1625549 reaction equation
[CH2:1]([N:4]1[C@H:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH2:15][C@H:7]2OS1(=O)=O)[C:2]#[CH:3].[F-:18].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:18][C@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@@H:8]1[NH:4][CH2:1][C:2]#[CH:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57789225HCID 57789225, compound

Product 1

HCID 57789264HCID 57789264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 100 mg (0.4 mmol) 8b in 2 ml dry THF was added 139 mg (0.44 mmol) tetrabutylammonium fluoride at 0° C. The reaction mixture was stirred for 90 min and concentrated. 2 ml 3N sulphuric acid was added and the solution was heated in microwave oven for 10 min. The solution was poured into 20 ml ice-cold and vigorously stirred 0.35 N sodium hydroxide solution. The aqueous phase was extracted with dichloromethane-isopropyl alcohol mixture (10:1) and the organic phase was dried over magnesium sulphate and concentrated. The residue The residue was purified by preparative HPLC to obtain the compound 8d as 14 mg amount batch

Workup

  1. concentrationconcentrated
  2. addition2 ml 3N sulphuric acid was added
  3. temperaturethe solution was heated in microwave oven for 10 min
  4. additionThe solution was poured into 20 ml ice-cold and vigorously stirred 0.35 N sodium hydroxide solution
  5. extractionThe aqueous phase was extracted with dichloromethane-isopropyl alcohol mixture (10:1)
  6. dry with materialthe organic phase was dried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue The residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b654eb1c167840bf8dfe8d0e43bb992f
Source dataset
uspto-grants-2014_07
Patent number
US08784775B2

Reaction notes

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