Tetrabutylammonium Fluoride → HCID 6540017, compound

HRID 227621Notes

Reaction equation

HRID 227621 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[C:9]([CH2:28][CH2:29][O:30][Si](C(C)(C)C)(C)C)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[C:9]([CH2:28][CH2:29][OH:30])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69059798HCID 69059798, compound

Product 1

HCID 6540017HCID 6540017, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 104C (92 mg, 0.17 mmol) in THF (5 mL) at room temperature was treated dropwise with a solution of 1M TBAF in THF (0.3 mL, 0.3 mmol), stirred overnight, and partitioned between water and ethyl acetate. The aqueous phase was extracted three times with ethyl acetate and the combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was recrystallized from dichloromethane to provide 54 mg (75%) of the desired product. MS(ESI) m/e 420 (M+H)+, 418 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (s, 3H); 2.75-2.80 (t, J=6.6 Hz, 2H); 3.54-3.60 (m, 2H); 4.85-4.89 (t, J=5.7 Hz, 1H); 6.79-6.82 (d, J=7.5 Hz, 2H); 7.14-7.19 (t, J=7.5 Hz, 1H); 7.24-7.32 (m, 4H); 7.61-7.63 (d, J=8.4 Hz, 2H); 8.26 (s, 1H); 8.67 (s, 1H); 8.87 (s, 1H); Anal. Calcd. for C22H21N5O2S.0.4H2O: C, 61.93; H, 5.15; N, 16.41. Found: C, 61.80; H, 4.95; N, 16.31.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialthe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-1b4f97564cef4cefbe0cd6ce8975de53
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

Loading…