Tetrahydrofuran → HCID 66726561, compound

HRID 710369Notes

Reaction equation

HRID 710369 reaction equation
[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([C:15]([O:17][NH:18][C:19]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[NH:26][CH:25]=[CH:24]5)=[NH:20])=O)=[CH:13][C:12]=3[O:32][CH3:33])[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:26]1[C:27]2[C:23](=[CH:22][C:21]([C:19]3[N:20]=[C:15]([C:14]4[CH:30]=[CH:31][C:11]([C:1]56[CH2:2][CH:3]7[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]7)[CH2:8]5)[CH2:10]6)=[C:12]([O:32][CH3:33])[CH:13]=4)[O:17][N:18]=3)=[CH:29][CH:28]=2)[CH:24]=[CH:25]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 178492750HCID 178492750, compound

Product 1

HCID 66726561HCID 66726561, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The suspension of the product of Step C (0.13 g; 0.293 mmol) and 1 M TBAF in THF (0.3 ml; 0.3 mmol) in anhydrous toluene (5 ml) was refluxed for 1 h under N2, cooled to room temperature and evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.12 g; 99%) as a colourless solid. 1H-NMR (CDCl3) 1.78 (s, 6H); 2.01-2.16 (m, 9H); 3.96 (s, 3H); 6.66 (m, 1H); 6.98 (d, 1H, J=8.6 Hz); 7.26 (m, 1H); 7.36 (d, 1H, J=8.14 Hz); 7.48 (d, 1H, J=8.14 Hz); 7.68 (d, 1H, J=1.6 Hz; 7.77 (dd, 1H, J=1.6, 8.1 Hz); 8.01 (dd, 1H, J=1.6, 8.1 Hz); 8.32 (broad s, 1H); 8.51 (s, 1H).

Workup

  1. temperaturewas refluxed for 1 h under N2
  2. customevaporated to dryness under reduced pressure
  3. customThe residue was purified by FCC (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-a36443c40f674708beffb24e6e8464f7
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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