Tetrabutylammonium Fluoride → HCID 15050935, compound

HRID 1110101Notes

Reaction equation

HRID 1110101 reaction equation
C[C:2](C)([O:29][SiH2]C(C)(C)C)[C:3]1[CH:28]=[CH:27][C:6]2[C:7](=[O:26])[NH:8][C:9]3[CH:25]=[CH:24][CH:23]=[N:22][C:10]=3[N:11]([C:12](=[O:21])[CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[C:5]=2[CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)(Cl)Cl.C1COCC1>[OH:29][CH2:2][C:3]1[CH:28]=[CH:27][C:6]2[C:7](=[O:26])[NH:8][C:9]3[CH:25]=[CH:24][CH:23]=[N:22][C:10]=3[N:11]([C:12](=[O:21])[CH2:13][N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131718523HCID 131718523, compound

Product 1

HCID 15050935HCID 15050935, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound l , 15 (15 mg, 0.03 mmol) was dissolved in 1 mL CHCl3, and a solution of 1M tetrabutylammonium fluoride in THF (40 μl) was added. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo, and the remaining residue was dissolved in saturated NaHCO washed with ether to remove non-polar impurities, and extracted with CHCl3. The CHCl3 extracts were combined, evaporated, and purified on a short silica gel column to yield 10 mg (86%) of 16 as a waxy solid: 1H NMR (CDCl3) δ 2.05-2.50 (m, 60 H), 2.20 (s, 3 H, CH3), 3.22 (d, J=14 Hz, 1 H), 3.60 (m, 1 H), 4.80 (s, 2 H, CH20), 7.30 (dd, J=7.8, 4.7 Hz, 1 H), 7.44 (d, J=8.1 Hz, 1 H), 7.50 (dd, J=1.6, 7.8 Hz, 1 H), 7.62 (s, 1 H), 7.96 (d, J=8.1 Hz, 1 H), 8.02 (m, 1 H); MS (CI/NH3) m/e 382 (MH+, base), 242, 141, 113.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe remaining residue was dissolved in saturated NaHCO
  3. washwashed with ether
  4. customto remove non-polar impurities
  5. extractionextracted with CHCl3
  6. customevaporated
  7. custompurified on a short silica gel column

Sources & evidence

ORD record
ord-fa47d71d62504763aa478a3afab2add1
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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