HCID 68161930, compound → HCID 1415873, compound

HRID 1892252Notes

Reaction equation

HRID 1892252 reaction equation
O[C:2]([C:12]1[C:13]([NH:18][C:19](=[O:24])[C:20](C)(C)C)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:11])CC(OC(C)(C)C)=O>Cl>[CH3:11][C:2]1[C:12]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[NH:18][C:19](=[O:24])[CH:20]=1

Participants

3

Reactant 1

HCID 68161930HCID 68161930, compound

Product 1

HCID 1415873HCID 1415873, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.3 g of tert-butyl 3-hydroxy-3-(2-pivalamidopyridin-3-yl)butanoate (3.9 mmol) in 2 mL 3N HCl was microwaved at 160° C. for 5 minutes. The resulting mixture was washed with Et2O (2×10 mL). The aqueous layer was basified using saturated K2CO3. The precipitate formed was filtered and washed with water to give 440 mg (71%) of the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.40 (d, J=1.17 Hz, 3 H) 6.43 (s, 1 H) 7.24 (dd, J=7.91, 4.69 Hz, 1 H) 8.12 (dd, J=7.91, 1.76 Hz, 1 H) 8.49 (dd, J=4.69, 1.76 Hz, 1 H) 11.92 (br. s., 1 H).

Workup

  1. washThe resulting mixture was washed with Et2O (2×10 mL)
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-dc41b7e0fbd141d98bdc44f985e6f5f8
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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