Tetrabutylammonium Fluoride → HCID 69280755, compound

HRID 1396237Notes

Reaction equation

HRID 1396237 reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][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][CH:15]3[CH:11]([N:12]=[C:13]([N:27]([CH2:35][CH2:36][CH3:37])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[S:14]3)[C@H:10]2[O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1.[Cl-].[Na+].O>[OH:19][CH2:18][C@H:17]1[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:27]([CH2:35][CH2:36][CH3:37])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32])[S:14]2)[C@@H:10]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)[C@@H:9]1[O:8][CH2:7][C:6]1[CH:48]=[CH:49][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86701098HCID 86701098, compound

Product 1

HCID 69280755HCID 69280755, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of tert-butyl (5R,6S,7R)-6,7-bis(4-methoxybenzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(propyl)carbamate (19 g, 26.50 mmol) in tetrahydrofuran (100 mL) was treated with TBAF (13.8 g, 53 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 10-30% ethyl acetate in petroleum ether to give compound 19 as a yellow oil (14.5 g, 91%). (ES, m/z): [M+H]+ 603.0; 1H NMR (300 MHz, CDCl3) 7.32-7.35 (d, J=8.7 Hz, 2H), 7.17-7.20 (d, J=8.7 Hz, 2H), 6.83-6.92 (m. 4H), 6.04-6.06 (d, J=6.9 Hz, 1H), 4.64-4.66 (m, 2H), 4.40-4.48 (m, 1H), 4.17-4.38 (m, 3H), 3.72-3.83 (m, 9H), 3.45-3.60 (m, 2H), 3.43-3.45 (m, 1H), 1.58-1.63 (m, 2H), 1.53 (s, 9H), 0.78-0.83 (t, J=7.2 Hz, 3H).

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 10-30% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-743631905b9945279b2fb2bf309dff24
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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