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

HRID 1092742Notes

Reaction equation

HRID 1092742 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 acid

Procedure

Compound 2 (6.0 g, 16.3 mmol) was treated with 4N HCl-dioxane (64 ml) for 1 h at room temperature. After the solvent was removed, the residue was extracted with EtOAc, washed with 5% citric acid and saturated NaCl. Then, the organic layer was dried over Na2SO4 and evaporated in vacuo to obtain compound 3. yield 2.6 g (76%); m.p. 150-155° 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 the solvent was removed
  2. extractionthe residue was extracted with EtOAc
  3. washwashed with 5% citric acid and saturated NaCl
  4. dry with materialThen, the organic layer was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b73526648c864d10af480db5b04daf48
Source dataset
uspto-grants-2012_03
Patent number
US08129527B2

Reaction notes

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