Tetrabutylammonium Fluoride → HCID 86595787, compound

HRID 1241447Notes

Reaction equation

HRID 1241447 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([CH2:17][C:18]3[N:19]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[S:21][CH:22]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([CH2:17][C:18]3[N:19]=[C:20]([CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[S:21][CH:22]=3)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86595785HCID 86595785, compound

Product 1

HCID 86595787HCID 86595787, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

(3S)-Ethyl 3-(1,3-benzodioxol-5-yl)-4-[2-(4-{[tert-butyl(diphenyl)silyl]oxy}butyl)-1,3-thiazol-4-yl]butanoate 6.55 g, 10.39 mmol) was dissolved in THF (20 mL) and tetrabutyl ammonium fluoride (1M, 23.39 mL, 23.39 mmol) was added. The reaction was stirred at ambient temperature for 2 hours. Dilute with diethyl ether, and wash with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and purified via silica gel chromatography (eluent: 4:1 Hexane:Ethyl Acetate) to give the product as a colorless oil. Yield: 3.08g (76%) 1H NMR (DMSO-d6) δ6.95–6.92 (m, 1H), 6.85–6.83 (m, 1H), 6.75–6.71 (m, 1H), 6.63–6.59 (m, 1H), 5.94 (s, 2H), 3.95–3.85 (q, 2H), 3.46–3.38 (m, 3H), 2.98–2.85 (m, 4H), 2.68–2.51 (m, 2H), 1.75–1.65 (m, 2H), 1.50–1.41 (m, 2H), 1.08–1.02 (t, 3H).

Workup

  1. washwash with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified via silica gel chromatography (eluent: 4:1 Hexane:Ethyl Acetate)

Sources & evidence

ORD record
ord-3b45f0cea6db4380abcf926583bbee4f
Source dataset
uspto-grants-2006_10
Patent number
US07115596B2

Reaction notes

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