Tetrabutylammonium Fluoride → HCID 68182914, compound

HRID 1615584Notes

Reaction equation

HRID 1615584 reaction equation
[N:1]1([C:7]2[S:15][C:14]3[S:13](=[O:17])(=[O:16])[N:12](COCC[Si](C)(C)C)[CH2:11][C:10]([C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=4)([OH:26])[C:9]=3[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:1]1([C:7]2[S:15][C:14]3[S:13](=[O:17])(=[O:16])[NH:12][CH2:11][C:10]([C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH:28]=4)([OH:26])[C:9]=3[CH:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68182917HCID 68182917, compound

Product 1

HCID 68182914HCID 68182914, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

6-(morpholin-4-yl)-4-(2-naphthyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (0.030 g, 0.055 mmol) was dissolved in THF (2.0 mL) and 1.00 M tetra-n-butylammonium fluoride in THF (0.549 mL, 0.549 mmol) was added. The solution was stirred at 40° C. overnight. The solvent was evaporated and the residue was purified using silica gel chromatography (12 g silica gel column, gradient 20% EA in hexane to 100% EA over 15 minutes) to give the product (14 mg, 55%). LCMS (FA) ES+: 417. 1H NMR (400 MHz, CD3OD) δ 7.94 (s, 1H), 7.86-7.83 (m, 3H), 7.50-7.47 (m, 2H), 7.39-7.36 (m, 1H), 5.66 (s, 1H), 5.48 (s, 1H), 3.96 (d, 1H), 3.73-3.70 (m, 4H), 3.62 (d, 1H), 3.09-3.05 (m, 4H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified
  3. customsilica gel chromatography (12 g silica gel column, gradient 20% EA in hexane to 100% EA over 15 minutes)

Sources & evidence

ORD record
ord-e5a00815dd9d46e8ba4c3da5f8e4371c
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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