Tetrabutylammonium Fluoride → HCID 18615146, compound

HRID 1265206Notes

Reaction equation

HRID 1265206 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]([C:28]2[CH:29]=[CH:30][C:31]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:32]([NH:34][S:35]([N:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])[CH:33]=2)[O:20][Si](CC)(CC)CC)[CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(O)(=O)C.C(OCC)(=O)C>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[C:3]([O:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]([C:28]2[CH:29]=[CH:30][C:31]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[C:32]([NH:34][S:35]([N:38]([CH3:40])[CH3:39])(=[O:36])=[O:37])[CH:33]=2)[OH:20])[CH:2]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18615195HCID 18615195, compound

Product 1

HCID 18615146HCID 18615146, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 60.1 mg of Intermediate 43 in 2.9 ml of anhydrous tetrahydrofuran, 36.8 μl of acetic acid and 574 μl of 1 M solution of tetrabutyl ammonium fluoride in tetrahydrofuran were added and the mixture was agitated at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and was washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution, followed by drying, whereupon the solvent was distilled off under a reduced pressure. The resulting residue was purified by a silica gel chromatography, whereupon the above-identified compound (50.0 mg) was obtained from eluted fractions with methanol/chloroform (7/100). Rf=0.39 (methanol/chloroform of 1/10).

Workup

  1. washwas washed with saturated aqueous sodium bicarbonate solution
  2. customby drying, whereupon the solvent
  3. distillationwas distilled off under a reduced pressure
  4. customThe resulting residue was purified by a silica gel chromatography, whereupon the above-identified compound (50.0 mg)
  5. customwas obtained
  6. washfrom eluted fractions with methanol/chloroform (7/100)

Sources & evidence

ORD record
ord-c8ded8ec269c4ab49f43411bf66b8a53
Source dataset
uspto-grants-2003_04
Patent number
US06545053B1

Reaction notes

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