Ethyl Acetate → HCID 86685120, compound

HRID 1055586Notes

Reaction equation

HRID 1055586 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@@H:8]1[C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:12]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:11]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@:10]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH3:56])=[C:50]([F:57])[C:49]=3[F:58])[CH:41]=2)([O:38][CH3:39])[O:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[CH2:15]([O:14][C@H:13]1[C@H:12]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:11]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@:10]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH3:56])=[C:50]([F:57])[C:49]=3[F:58])[CH:41]=2)([O:38][CH3:39])[O:9][C@@H:8]1[CH2:7][OH:6])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 89576927HCID 89576927, compound

Product 1

HCID 86685120HCID 86685120, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 23i (16.29 g, 18.95 mmol) in tetrahydrofuran (100 mL) was added tetrabutylammonium fluoride (37.9 mL, 37.9 mmol, 1 M in tetrahydrofuran) at room temperature. The mixture was stirred at room temperature for 12 hours, and then ethyl acetate (200 mL) was added. The resulting mixture was washed with saturated aqueous sodium chloride (100 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=15/1 to give the title compound 23j as a yellow solid (4.42 g, 31%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.29 (m, 10H), 7.22 (s, 2H), 7.5 (m, 4H), 6.95 (m, 2H), 6.76 (m, 1H), 6.51 (m, 1H), 4.92 (m, 3H), 4.66 (d, 1H), 4.47 (d, 1H), 4.14 (m, 1H), 4.03 (m, 3H), 3.88 (m, 3H), 3.77 (m, 1H), 3.66 (m, 2H), 3.27 (d, 1H), 3.05 (s, 3H), 1.39 (t, 3H).

Workup

  1. washThe resulting mixture was washed with saturated aqueous sodium chloride (100 mL×3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography
  6. washeluted with PE/EtOAc(v/v)=15/1

Sources & evidence

ORD record
ord-5e8e5241fa724a24b24a8429d3973301
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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