Sodium Hydroxide → (4-{3-[1-(4-tert-Butyl-phenyl)-ethylideneaminooxy]-propoxy}-phenyl)-acetic Acid

HRID 29640Notes

Reaction equation

HRID 29640 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)[CH3:18])=[CH:7][CH:6]=1.[OH-].[Na+]>O1CCCC1.C(O)C>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:17](=[N:16][O:15][CH2:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:29])=[O:2])=[CH:10][CH:9]=2)[CH3:18])=[CH:24][CH:23]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86597381(4-{3-[1-(4-Tert-butyl-phenyl)-ethylideneaminooxy]-propoxy}-phenyl)-acetic acid methyl ester

Product 1

HCID 72975664(4-{3-[1-(4-tert-Butyl-phenyl)-ethylideneaminooxy]-propoxy}-phenyl)-acetic AcidYield 46%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of (4-{3-[1-(4-tert-butyl-phenyl)-ethylideneaminooxy]-propoxy}-phenyl)-acetic acid methyl ester (3.55 mmol) in tetrahydrofuran/ethanol (3/2) (20 mL) was added 1 M sodium hydroxide solution (6 mL, 6 mmol) and the reaction was stirred overnight at room temperature. It was concentrated to a small volume, acidified to pH 1 with 1M hydrochloric acid solution and extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80)+1% formic acid to afford the title compound (0.620 g, 46%) as a light yellow solid. mp=98.7-99.7° C.; mass spectrum (−ESI, M−H) m/z 382. 1H NMR (400 MHz, DMSO-d6); δ 12.20 (bs, 1H), 7.55 (d, 2H), 7.38 (d, 2H). 7.14 (d, 2H), 6.87 (d, 2H), 4.25 (t, 2H), 4.05 (t, 2H), 3.47 (s, 2H), 2.16 (s, 3H), 2.09 (m, 2H), 1.25 (s, 9H). Elemental analysis: Calcd. for C23H29NO4: C, 72.04; H, 7.62; N, 3.65, Found: C, 71.43; H, 7.87; N, 3.52.

Workup

  1. concentrationIt was concentrated to a small volume
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fbb86cff19b44c0f933b166c97753899
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Reaction notes

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