Tetrahydrofuran → HCID 131733836, compound

HRID 708524Notes

Reaction equation

HRID 708524 reaction equation
[Si]([O:18][CH:19]([C:21]1[CH:25]=[N:24][N:23]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:34])[O-:33])[C:29](=[O:35])[NH:28]2)[N:22]=1)[CH3:20])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:36][CH2:37][CH2:38]C[N+](CCCC)(CCCC)CCCC.[F-].[CH2:54]1[CH2:58]O[CH2:56][CH2:55]1>>[OH:18][CH:19]([C:21]1[CH:25]=[N:24][N:23]([CH2:26][C@@H:27]2[C@H:30]([NH:31][C:32](=[O:34])[O:33][CH2:56][C:55]3[CH:38]=[CH:37][CH:36]=[CH:58][CH:54]=3)[C:29](=[O:35])[NH:28]2)[N:22]=1)[CH3:20]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131733837HCID 131733837, compound

Product 1

HCID 131733836HCID 131733836, compoundYield 56%

Procedure

A mixture of ((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (1.35 g, 2.31 mmol) and TBAF (1 M in THF, 4.63 ml, 4.63 mmol) in THF (23 ml) was stirred at room temperature 3 h. The solvent was removed and the residue was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound (450 mg, 56%) as a light yellow solid. LCMS: Rt=0.53 min, m/z=346.1 (M+1) Method 2m_acidic.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified via silica gel chromatography (EtOAc-Heptane)

Sources & evidence

ORD record
ord-c967ca3b111e4703bd40b0f66dbb2b12
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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