Tetrahydrofuran → HCID 66726760, compound

HRID 710364Notes

Reaction equation

HRID 710364 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[C:14]([O:16][NH:17][C:18]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[NH:19])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1(C)C=CC=CC=1>[NH:25]1[C:26]2[C:22](=[CH:21][C:20]([C:18]3[N:19]=[C:14]([C:13]4[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:11]([C:1]56[CH2:10][CH:5]7[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]7)[CH2:2]5)[CH2:8]6)[CH:12]=4)[O:16][N:17]=3)=[CH:28][CH:27]=2)[CH:23]=[CH:24]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 178491634HCID 178491634, compound

Product 1

HCID 66726760HCID 66726760, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of the product of Step C (0.16 g; 0.36 mmol) and 1 M TBAF in THF (0.3 ml; 0.3 mmol) in anhydrous toluene was refluxed for 1 h under reduced pressure, cool to room temperature and evaporated to dryness under reduced pressure. The residue was diluted to 15 ml with EtOAc, washed with water, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by crystallization from hexane/EtOAc to give the title compound (0.16 g; 100%) as colourless solid. 1H-NMR (CDCl3) 1.79 (s, 6H); 2.0-2.16 (m, 9H); 3.92 (s, 3H); 6.66 (s, 1H); 6.98 (d, 1H, J=8.6 Hz); 7.26 (m, 1H); 7.48 (d, 1H, J=8.5 Hz); 7.9-8.11 (m, 2H); 8.29 (broad s, 1H); 8.51 (s, 1H).

Workup

  1. temperaturewas refluxed for 1 h under reduced pressure
  2. customevaporated to dryness under reduced pressure
  3. additionThe residue was diluted to 15 ml with EtOAc
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. customthe residue was purified by crystallization from hexane/EtOAc

Sources & evidence

ORD record
ord-968df20ca85546bc8bfc8964cccbab1a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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