Sodium Hydroxide → 5-(3-(((1-acetylpiperidin-4-yl)carbonyl)amino)phenyl)isoxazole-3-carboxylic Acid

HRID 1375662Notes

Reaction equation

HRID 1375662 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]3[O:23][N:22]=[C:21]([C:24]([O:26]CC)=[O:25])[CH:20]=3)[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]3[O:23][N:22]=[C:21]([C:24]([OH:26])=[O:25])[CH:20]=3)[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69507772Ethyl 5-(3-{((1-acetylpiperidin-4-yl)carbonyl)amino}phenyl)isoxazole-3-carboxylate

Product 1

HCID 99984345-(3-(((1-acetylpiperidin-4-yl)carbonyl)amino)phenyl)isoxazole-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(3-{((1-acetylpiperidin-4-yl)carbonyl)amino}phenyl)isoxazole-3-carboxylate (68 g) was dissolved in THF (1.2 mL)and treated with 1N NaOH solution (1 mL) at ambient temperature for 2 hours, THF was removed under vacuo and 1N HCl was added. The mixture was extracted with ethyl acetate, dried with anhydrous Na2SO4, filtered, concentrated under vacuo to provide the title compound. MS (ESI(+)) m/e 258 (M+H)+, 375 (M+NH4)+, 380 (M+Na)+; 1H NMR (500 MHz, DMSO-d6) δ 10.14 (s, 1H), 8.20 (s, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=8.1 Hz), 7.47 (t, 1H, J=8.0 Hz), 7.20 (s, 1H), 4.40 (br d, 1H, J=12.8 Hz), 3.88 (br d, 1H, J=13.4 Hz), 3.08 (br t, 1H, J=12.9 Hz), 2.60 (m, 2H), 2.01 (s, 3H), 1.84 (m, 2H), 1.60 (m, 1H, 1.44 (m, 1H).

Workup

  1. customTHF was removed under vacuo and 1N HCl
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-e196ca1e27ae4a3fbe39c4dc1a100294
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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