1,4-Dioxane hydrochloride → 3-(5-tert-Butyloxazol-4-yl)-2-hydroxyacrylic acid

HRID 15395Notes

Reaction equation

HRID 15395 reaction equation
C([O:5][C:6]([C:8](NC(=O)OC(C)(C)C)=[CH:9][C:10]1[N:11]=[CH:12][O:13][C:14]=1[C:15]([CH3:18])([CH3:17])[CH3:16])=[O:7])(C)(C)C.Cl.[O:28]1CCOCC1>>[C:15]([C:14]1[O:13][CH:12]=[N:11][C:10]=1[CH:9]=[C:8]([OH:28])[C:6]([OH:5])=[O:7])([CH3:18])([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 72404735tert-Butyl 1-(tert-butoxycarbonyl)-2-(5-tert-butyloxazol-4-yl)vinylcarbamate

Product 1

HCID 665900433-(5-tert-Butyloxazol-4-yl)-2-hydroxyacrylic acidYield 76%

Procedure

The compound from Example 5 (6.0 g, 16.3 mmol) was treated with 4N HCl-dioxane (64 mL) for 1 h at room temperature. After removal of the solvent, the residue was dissolved in AcOEt, washed with 5% citric acid and saturated NaCl, dried over Na2SO4, and concentrated in vacuo to obtain 2.6 g (76%) of the title compound as a white solid: mp 153-155° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.59 (s, 1H), 6.55 (s, 1H), 1.36 (s, 1H); m/z 211.0841 (M+) (calcd for C10H13NO4: 211.0844).

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in AcOEt
  3. washwashed with 5% citric acid and saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-443f7411c40d480798eda622baaa5d6e
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Reaction notes

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