Hydrochloric Acid → HCID 67408131, compound

HRID 1913414Notes

Reaction equation

HRID 1913414 reaction equation
C([O:5][C:6](=[O:18])[CH:7](C#N)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][N:9]=1)(C)(C)C.Cl>O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:18])=[O:5])=[N:9][CH:10]=1)[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67408263HCID 67408263, compound

Product 1

HCID 67408131HCID 67408131, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
104 °C

Procedure

Cyano-(5-ethyl-pyridin-2-yl)-acetic acid tert-butyl ester (7.3 g) was mixed with 70 mL of water and 70 mL of 12N HCl and was heated at 104° C. for 3 hours before removing the volatiles in vacuo. Water was added to dissolve the solids and the pH of the solution was adjusted to 9-10 with 2N NaOH. The solution was washed with 2-methylTHF (2×). The aqueous solution was adjusted to pH 4 with 2N HCl and was concentrated under vacuum to an oily solid. The residue was triturated with hot chloroform and heptanes to afford (5-ethylpyridin-2-yl)acetic acid (SM-1ac) as a tan solid (3.88 g, 31%, 3 steps). MS (ES+) 166.1 (M+H)+. 1H NMR (DMSO-d6) δ 1.16 (t, 3H), 2.57 (q, 2H), 3.66 (s, 2H), 7.22 (d, 1H), 7.56 (dd, 1H), 8.31 (d, 1H), 12.44 (br s, 1H).

Workup

  1. custombefore removing the volatiles in vacuo
  2. additionWater was added
  3. dissolutionto dissolve the solids
  4. washThe solution was washed with 2-methylTHF (2×)
  5. concentrationwas concentrated under vacuum to an oily solid
  6. customThe residue was triturated with hot chloroform and heptanes

Sources & evidence

ORD record
ord-d6af2b421568465d961fb9ca6af53cff
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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