tert-Butanol → HCID 86731411, compound

HRID 2277323Notes

Reaction equation

HRID 2277323 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:16][N:17]=1)C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:42]([CH2:46]C)C(C)C)(C)C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:42][C:46](=[O:29])[O:52][C:48]([CH3:51])([CH3:50])[CH3:49])[C:15]([O:18][CH2:19][O:20][CH3:21])=[CH:16][N:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86731410HCID 86731410, compound

Product 1

HCID 86731411HCID 86731411, compound

Procedure

To a solution of 2-(benzyloxy)-5-(methoxymethoxy)isonicotinic acid (9.20 g) in tert-butyl alcohol (30 mL) were added diphenylphosphoryl azide (26.3 mL) and N,N-diisopropylethylamine (13.3 mL), and the mixture was stirred at room temperature for 1 hr, and then with refluxing at 80° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (11.4 g).

Workup

  1. temperaturewith refluxing at 80° C. for 3 hr
  2. temperatureto cool to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the residue was added water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe combined organic layer were washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3dd0fd2cbee744cc9ec1fafd855f8e66
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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