Tetrabutylammonium Fluoride → (2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide

HRID 627143Notes

Reaction equation

HRID 627143 reaction equation
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([C:23]([NH2:25])=[O:24])=[CH:8][C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([C:23]([NH2:25])=[O:24])=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89852439(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide2×

Product 1

HCID 89854131(2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamideYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-4-carboxamide (Intermediate 108, 450 mg, 1.2 mmol) was dissolved in THF (about 7 mL); the atmosphere in the reaction vessel was evacuated and backfilled with argon, and the solution was stirred in an ice bath for ten minutes. To it was then added tetrabutylammonium fluoride (1 M in THF) (1.5 mL, 1.5 mmol) dropwise. After one hour, analysis of the mixture by LCMS indicated consumption of starting material and formation of one major product. The mixture was concentrated and dissolved in methylene chloride. Normal-phase chromatography (0-10% methanol in methylene chloride, 25-g column, 25 minutes) was used to isolate the desired product (284 mg, 92%, white solid).

Workup

  1. customthe atmosphere in the reaction vessel was evacuated
  2. customconsumption of starting material and formation of one major product
  3. concentrationThe mixture was concentrated
  4. dissolutiondissolved in methylene chloride
  5. customNormal-phase chromatography (0-10% methanol in methylene chloride, 25-g column, 25 minutes)

Sources & evidence

ORD record
ord-9ba7b1bf69db47c58e5a7e86f6b9095d
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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