Tetrabutylammonium Fluoride → HCID 69083734, compound

HRID 1396231Notes

Reaction equation

HRID 1396231 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:17]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[O:16][C@H:15]3[C@H:11]([N:12]=[C:13]([N:27]([CH3:29])[CH3:28])[S:14]3)[C@H:10]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[CH3:29][N:27]([CH3:28])[C:13]1[S:14][C@H:15]2[O:16][C@H:17]([CH2:18][OH:19])[C@@H:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:41][CH:40]=3)[C@H:10]([O:30][CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)[C@H:11]2[N:12]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69085628HCID 69085628, compound

Product 1

HCID 69083734HCID 69083734, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(3aR,5R,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-N,N-dimethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine (9.5 g, 15.8 mmol) in THF (100 mL) was treated with TBAF (8.27 g, 31.6 mmol) overnight at room temperature. The resulting solution was diluted with brine (200 mL), extracted with ethyl acetate (2×200 mL), and dried over anhydrous magnesium sulfate. After removal of solvents, the residue was purified by silica gel column, eluted with 1-2.5% MeOH in dichloromethane to give compound 10 as a yellow oil (7.0 g, 86%). (ES, m/z): [M+H]+ 489.0; 1H NMR (300 MHz, CDCl3) δ 7.32-7.62 (m, 2H), 7.22-7.28 (m, 2H), 6.85-6.91 (m, 4H), 6.26-6.28 (d, J=6.6 Hz, 1H), 4.52-4.73 (m, 4H), 4.31-4.34 (d, J=11.4 Hz, 1H), 4.23 (s, 1H), 181 (s, 6H), 3.53-3.76 (m, 4H), 3.01 (m, 6H), 1.78-1.82 (m, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removal of solvents
  4. customthe residue was purified by silica gel column
  5. washeluted with 1-2.5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-00cc4166d819454ab2f44037aedbf4d0
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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