Tetrabutylammonium Fluoride → HCID 67284230, compound

HRID 1907100Notes

Reaction equation

HRID 1907100 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][Si](C(C)(C)C)(C)C)[O:8][C@@H:7]([N:19]2[CH:26]=[C:25]([I:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:6]1)[CH:2]=[CH2:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][OH:11])[O:8][C@@H:7]([N:19]2[CH:26]=[C:25]([I:27])[C:23](=[O:24])[NH:22][C:20]2=[O:21])[CH2:6]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67283601HCID 67283601, compound

Product 1

HCID 67284230HCID 67284230, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (34) (2.34 g, 4.71 mmol) in dry THF (40 ml) was added at 0° C. TBAF (5.2 ml, 5.2 mmol, 1 M solution in THF). The reaction mixture was allowed to warm up to room temperature and was then stirred for 16 h. The reaction was quenched by adding sat. NaCl solution (20 ml) and extracted with EtOAc three times. The combined organic layers were dried over MgSO4. The crude mixture was purified by chromatography on silica (EtOAc:petrol 7:3). Product (35) (1.4 g, 75%) was isolated as a colourless solid. 1H NMR (d6 DMSO) δ 2.02-2.39 (m, 2H, H-2′), 3.42-3.52 (m, 2H, H-5′), 3.84-3.88 (m, 3H, H-4′, CH2], 3.97-4.00 (m, 1H, H-3′), 5.02-5.09 (m, 2H, OH, ═CH2), (dd, J=1.9, 17.3 Hz, 1H, ═CH2), 5.73-5.82 (m, 1H, CH═), 5.94 (t, J=6.8 Hz, 1H, H-1′), 8.24 (s, 1H, H-6), 11.56 (s, 1H, NH). Mass (−ve electrospray) calcd for C12H16IN2O5 394.0. Found 393.

Workup

  1. customThe reaction was quenched
  2. additionby adding sat. NaCl solution (20 ml)
  3. extractionextracted with EtOAc three times
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customThe crude mixture was purified by chromatography on silica (EtOAc:petrol 7:3)

Sources & evidence

ORD record
ord-910f0ffe75514358b5b33200ee162858
Source dataset
uspto-grants-2013_12
Patent number
US08597881B2

Reaction notes

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