tert-Butanol → HCID 67465458, compound

HRID 2368113Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10](C(O)=O)[C:9]([O:15][CH2:16][O:17][CH3:18])=[CH:8][N:7]=2)[CH2:3][CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:39]([CH2:43]C)C(C)C)(C)C.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([NH:39][C:43](=[O:26])[O:49][C:45]([CH3:48])([CH3:47])[CH3:46])[C:9]([O:15][CH2:16][O:17][CH3:18])=[CH:8][N:7]=2)[CH2:2][CH2:3]1

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 81531Diisopropylethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 57517502HCID 57517502, compound

Product 1

HCID 67465458HCID 67465458, compound

Procedure

To a solution of 2-(cyclopropylmethoxy)-5-(methoxymethoxy)pyridine-4-carboxylic acid (810 mg) in tert-butyl alcohol (16 mL) were added diphenylphosphorylazide (0.831 mL) and N,N-diisopropylethylamine (0.669 mL), and the mixture was refluxed for 11 hr. The solvent was evaporated under reduced pressure, brine was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (737 mg).

Workup

temperaturethe mixture was refluxed for 11 hr
customThe solvent was evaporated under reduced pressure, brine
additionwas added
extractionthe mixture was extracted with ethyl acetate
washThe obtained organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-070f083341994e52959c40171c9ca67f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703758B2

Reaction notes

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