Tetrabutylammonium Fluoride → HCID 131733850, compound

HRID 708538Notes

Reaction equation

HRID 708538 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:24]([CH2:25][NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-:38])=[O:37])(=[O:29])=[O:28])=[N:23][N:22]([CH2:39][C@@H:40]2[C@H:43]([NH:44][C:45](=[O:54])[O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42](=[O:55])[N:41]2[CH2:56][C:57]2[CH:62]=[CH:61][C:60]([O:63][CH3:64])=[CH:59][C:58]=2[O:65][CH3:66])[N:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH3:66][O:65][C:58]1[CH:59]=[C:60]([O:63][CH3:64])[CH:61]=[CH:62][C:57]=1[CH2:56][N:41]1[C:42](=[O:55])[C@@H:43]([NH:44][C:45](=[O:54])[O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C@H:40]1[CH2:39][N:22]1[N:21]=[C:20]([CH2:19][OH:18])[C:24]([CH2:25][NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-:38])=[O:37])(=[O:28])=[O:29])=[N:23]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131733848HCID 131733848, compound

Product 1

HCID 131733850HCID 131733850, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-((2-nitrophenylsulfonamido)methyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate (252 mg, 0.270 mmol) in THF (2.8 mL) at 0° C. was added TBAF (1.0 M in THF, 270 μL, 0.270 mmol). After stirring for 2.6 h, the solution was diluted with EtOAc and partially concentrated in vacuo. Additional EtOAc was added along with KHSO4 (2%, aq) and water. The layers were separated and the aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-100%), affording the title compound (165 mg, 88%) as a white solid. Rt=0.83 min, m/z=696.3 (M+1) Method 2m_acidic.

Workup

  1. concentrationpartially concentrated in vacuo
  2. additionAdditional EtOAc was added along with KHSO4 (2%, aq) and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-100%)

Sources & evidence

ORD record
ord-a0f8b33cf5d147d6a6c29e0d793c9198
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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