Tetrabutylammonium Fluoride → HCID 178470375, compound

HRID 1696648Notes

Reaction equation

HRID 1696648 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][N:14]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[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][N:14]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])[CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178470378HCID 178470378, compound

Product 1

HCID 178470375HCID 178470375, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-tert-Butyloxy-9-{5-[5-(tert-butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-yl}-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester (0.5 g, 0.71 mmol) is treated with tetra-N-butylammonium fluoride (0.185 g, 0.71 mmol) in tetrahydrofuran (5 ml) for 4 hours at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is purified on a silica gel 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 solid obtained is washed with actonitrile (30 ml), pentane (30 ml) and dried under vacuum to yield 270 mg of 6-tert-butyloxy-9-[5-(5-Hydroxy-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester. Yield=64%. Analytical LC/MS (method B): retention time=3.34 min., m/z=592.31 (positive ion mode).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified on a silica gel 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. customthe solid obtained
  7. washis washed with actonitrile (30 ml), pentane (30 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-798962dec6464b5ead18007c3d9f355d
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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