tert-Butanol → HCID 45092150, compound

HRID 1784930Notes

Reaction equation

HRID 1784930 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7]C(O)=O)[O:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.C([N:30]([CH2:33]C)CC)C.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][NH:30][C:33](=[O:18])[O:39][C:35]([CH3:38])([CH3:37])[CH3:36])[O:4][N:3]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acid

Product 1

HCID 45092150HCID 45092150, compoundYield 10%

Procedure

A solution of 321 mg (2.27 mmol) of 2-(3-methylisoxazol-5-yl)acetic acid, 0.5 mL (2.32 mmol) of diphenylphosphorylazide (DPPA), and 0.35 mL (2.51 mmol) of triethylamine in 30 mL of distilled tert-butyl alcohol was refluxed for 13.5 hours. The solution was concentrated, and the crude residue was dissolved in EtOAc. The organic layer was washed with 1N HCl (3×10 mL) and saturated NaHCO3 solution (3×10 mL). The organic layer was dried over sodium sulfate, filtered, concentrated. Purification by flash silica gel chromatography (28% EtOAc/hexanes) provided 50 mg (10% yield) of tert-butyl (3-methylisoxazol-5-yl)methylcarbamate as a pale yellow solid.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe crude residue was dissolved in EtOAc
  3. washThe organic layer was washed with 1N HCl (3×10 mL) and saturated NaHCO3 solution (3×10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (28% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b687ac30e4d84a9bac08ed01851f123f
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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