Tetrabutylammonium Fluoride → HCID 59347043, compound

HRID 1697249Notes

Reaction equation

HRID 1697249 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[O:14][C:13]([CH3:16])([CH3:15])[N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:11]1[CH2:24][C:25]1[CH:30]=[C:29]([CH3:31])[N:28]=[C:27]([Cl:32])[CH:26]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:32][C:27]1[CH:26]=[C:25]([CH2:24][C@H:11]2[C@@H:10]([CH2:9][OH:8])[O:14][C:13]([CH3:16])([CH3:15])[N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:30]=[C:29]([CH3:31])[N:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86614126(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 59347043HCID 59347043, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(4S,5S)-Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-4-((2-chloro-6-methylpyridin-4-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (0.206 g, 0.425 mmol) was dissolved in THF (4 mL) and cooled to 0° C. TBAF (0.637 ml, 0.637 mmol) was added to the mixture dropwise and the reaction was stirred 1 hr and then quenched with saturated ammonium chloride and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated. The crude material was purified by silica column chromatography (19:1 DCM/MeOH) and then reverse phase HPLC to give the title compound. MS m/z: 371.3 (100%, M+1).

Workup

  1. customquenched with saturated ammonium chloride
  2. additiondiluted with EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe crude material was purified by silica column chromatography (19:1 DCM/MeOH)

Sources & evidence

ORD record
ord-9dd4917a1eef4a96aab65ca2ef5b611a
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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