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

HRID 29640노트

반응식

HRID 29640 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbb86cff19b44c0f933b166c97753899
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

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