Tetrahydrofuran → HCID 59737241, compound

HRID 1907719Notes

Reaction equation

HRID 1907719 reaction equation
[Si]([O:18][CH2:19][C:20]1[S:24][C:23]([C:25]2[CH:26]=[CH:27][C:28]([N+:42]([O-:44])=[O:43])=[C:29]([NH:31][C:32](=[O:41])[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH:30]=2)=[CH:22][CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>CCOC(C)=O>[OH:18][CH2:19][C:20]1[S:24][C:23]([C:25]2[CH:26]=[CH:27][C:28]([N+:42]([O-:44])=[O:43])=[C:29]([NH:31][C:32](=[O:41])[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH:30]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59737377HCID 59737377, compound

Product 1

HCID 59737241HCID 59737241, compoundYield 193.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 189 (0.673 g, 1.08 mmol) in a 1M solution of tetrabutylammonium fluoride in THF (1.5 mL, 1.5 mmol) was stirred for 90 min at room temperature. The reaction mixture was diluted with AcOEt, washed with 5% KHSO4, water, dried over MgSO4, filtered and concentrated to give a solid material which was triturated with DCM, to afford title compound 190 (0.805 g, 75% yield). The supernatant was collected, evaporated and the residue was purified by flash column chromatography (eluent: 50% AcOEt in DCM) to afford additional amount of 190 (0.161 g, 15% yield).

Workup

  1. washwashed with 5% KHSO4, water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid material which
  6. customwas triturated with DCM

Sources & evidence

ORD record
ord-114616c126d84b0c93642a4aff7d3caf
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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