Tetrabutylammonium Fluoride → HCID 140695600, compound

HRID 708419Notes

Reaction equation

HRID 708419 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12](/[C:14](=[N:33]/[O:34][C:35]([CH3:44])([CH3:43])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])/[C:15](=[O:32])[NH:16][C@H:17]2[C@@H:20]([CH2:21][N:22]3[CH:26]=[C:25]([Si](C)(C)C)[N:24]=[N:23]3)[NH:19][C:18]2=[O:31])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[N:22]1([CH2:21][C@@H:20]2[C@H:17]([NH:16][C:15](=[O:32])/[C:14](=[N:33]\[O:34][C:35]([CH3:44])([CH3:43])[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])/[C:12]3[N:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[S:10][CH:11]=3)[C:18](=[O:31])[NH:19]2)[CH:26]=[CH:25][N:24]=[N:23]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 140689318HCID 140689318, compound

Product 1

HCID 140695600HCID 140695600, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the method described in WO2013/028590. To a solution of tert-butyl 2-(((Z)-(1-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)-2-oxo-2-(((3S,4R)-2-oxo-4-((4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)methyl)azetidin-3-yl)amino)ethylidene)amino)oxy)-2-methylpropanoate (140 mg, 0.261 mmol) in THF (4 mL) was added TBAF (1 M in THF, 860 μL, 0.86 mmol). After stirring at rt for 16 h, additional TBAF (1M in THF, 1.0 mL, 1.0 mmol) was added. After stirring for an another 48 h, the solution was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 7%) affording the title compound (84 mg, 68%) as an off white solid. LCMS: m/z=579.2 (M+1).

Workup

  1. customPrepared
  2. stirringAfter stirring for an another 48 h
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 7%)

Sources & evidence

ORD record
ord-e9d542f3cee8471e9f081ef94b61eb37
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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