Tetrabutylammonium Fluoride → HCID 178470351, compound

HRID 1696621Notes

Reaction equation

HRID 1696621 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]2[CH:18]([C:19]3[O:20][C:21]([S:24][C:25]4[NH:29][C:28]5[CH:30]=[CH:31][C:32]([O:34][Si](C(C)(C)C)(C)C)=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:42])[CH2:15][CH2:14][CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]2[CH:18]([C:19]3[O:20][C:21]([S:24][C:25]4[NH:29][C:28]5[CH:30]=[CH:31][C:32]([OH:34])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:42])[CH2:15][CH2:14][CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178470355HCID 178470355, compound

Product 1

HCID 178470351HCID 178470351, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-{5-[5-(tert-Butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-yl}-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester (376 mg, 0.62 mmol) is treated with tetra-N-butylammonium fluoride (162 mg 0.62 mmol) in tetrahydrofuran (5 ml) for 5 hours at room temperature. The reaction mixture is then concentrated under reduced pressure and the residue is purified on a silicagel column (40 g) eluted with a mixture of dichloromethane and methanol (9/1, v/v). The fractions containing the expected product are concentrated under reduced pressure and the residue is washed with acetonitrile (20 ml), pentane (20 ml), diisopropylether (20 ml) and dried under vacuum to yield 154 mg of 9-[5-(5-hydroxy-1H-benzoimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester as a light yellow powder. Yield=50%. Analytical LC/MS (method C): m/z=489 (negative ion mode [M−H]−), m/z=491 (positive ion mode [M+H]+).

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure
  2. customthe residue is purified on a silicagel column (40 g)
  3. washeluted with a mixture of dichloromethane and methanol (9/1
  4. additionThe fractions containing the expected product
  5. concentrationare concentrated under reduced pressure
  6. washthe residue is washed with acetonitrile (20 ml), pentane (20 ml), diisopropylether (20 ml)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e435bf098bd744b88424de940cbf8aad
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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