Acetic Acid → HCID 74767505, compound

HRID 1486768Notes

Reaction equation

HRID 1486768 reaction equation
[Si]([O:8][C@H:9]([C:11]1[N:15]([C:16]2[N:21]=[C:20]([CH3:22])[N:19]=[C:18]([C@@H:23]3[CH2:25][C@H:24]3[C:26]3[N:30]([CH3:31])[C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[N:27]=3)[CH:17]=2)[N:14]=[C:13]([CH3:36])[N:12]=1)[CH3:10])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:36][C:13]1[N:12]=[C:11]([C@@H:9]([OH:8])[CH3:10])[N:15]([C:16]2[CH:17]=[C:18]([C@@H:23]3[CH2:25][C@H:24]3[C:26]3[N:30]([CH3:31])[C:29]4[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=4[N:27]=3)[N:19]=[C:20]([CH3:22])[N:21]=2)[N:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium Fluoride2×HCID 90166363HCID 90166363, compound

Product 1

HCID 74767505HCID 74767505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13-1 (2.8 g, 5.6 mmol), acetic acid (0.41 ml, 7.2 mmol) and 1 N tetrabutylammonium fluoride (7.8 mL, 7.8 mmol) in THF (15.6 ml) was stirred at 23° C. for 16 h. Additional 1 N tetrabutylammonium fluoride in THF (4 mL, 4 mmol) was added and stirring was continued for 16 h. The white precipitate that formed was collected by filtration, washed with THF (2×50 mL) followed by ether (2×50 mL). The white solid was dissolved in DCM (100 mL) and washed with saturated aqueous sodium bicarbonate solution (2×100 mL), brine (2×100 mL) and water (2×100 mL) successively. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford a clear oil. The oil was triturated from 5:1 ether/EtOAc and the resulting white solid was collected by filtration and air dried to provide Example 13. 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H), 7.71-7.69 (m, 1H), 7.32-7.24 (m, 3H), 6.12 (d, 1H, J=5.4 Hz), 5.19-5.17 (m, 1H), 3.83 (s, 3H), 2.89-2.86 (m, 2H), 2.73 (s, 3H), 2.44 (s, 3H), 2.09-2.00 (m, 2H), 1.73 (d, 3H, J=6.6 Hz); MS: m/z=390.3 (M+H).

Workup

  1. customThe white precipitate that formed
  2. filtrationwas collected by filtration
  3. washwashed with THF (2×50 mL)
  4. dissolutionThe white solid was dissolved in DCM (100 mL)
  5. washwashed with saturated aqueous sodium bicarbonate solution (2×100 mL), brine (2×100 mL) and water (2×100 mL) successively
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a clear oil
  10. customThe oil was triturated from 5:1 ether/EtOAc
  11. filtrationthe resulting white solid was collected by filtration and air
  12. customdried
  13. customto provide Example 13

Sources & evidence

ORD record
ord-e228b0222fc34956aeaa84336591b2da
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

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