3-[4-Hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl ester → Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate

HRID 1181039노트

반응식

HRID 1181039 반응식
[C:1]([O:5][C:6](=[O:19])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH:16]=[N:17]O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:16][NH2:17])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 724795743-[4-Hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 17984622Tert-butyl-3-[2-(aminomethyl)-4-hydroxyphenyl]propanoate수율 40%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 3-[4-hydroxy-2-(hydroxyimino-methyl)-phenyl]-acrylic acid tert-butyl ester (0.50 g, 1.9 mmol) in ethanol (50 mL) was treated with 10% palladium on carbon (0.25 g). The resulting suspension was treated with hydrogen using a Parr shaker apparatus at ambient temperature and 50 psi for 16 h. The reaction mixture was filtered through Celite, rinsed with ethanol (20 mL), and concentrated. The residue was dissolved in ethyl acetate (50 mL) and washed with 10% K2CO3 solution (2×25 mL) and 1N NaOH (2×25 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was crystallized from isopropyl acetate to give the title compound (0.14 g, 40%), mp 154-157° C. 1H NMR (CD3OD): δ 1.37 (s, 9H), 2.44-2.50 (t, 2H), 2.80-2.85 (t, 2H), 3.75 (s, 2H), 4.83 (s, 3H), 6.57-6.63 (dd, 1H), 6.75-6.77 (d, 1H), 6.95-7.00 (d, 1H). MS (ES+) m/z 252.1 ([M+H]+). MS (ES−) m/z 250.2 ([M−H]−). Anal. Calculated for C14H21NO3: C: 66.9069; H: 8.4222; N: 5.5731. Found: C: 66.57; H: 8.29; N: 5.60.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. washrinsed with ethanol (20 mL)
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with 10% K2CO3 solution (2×25 mL) and 1N NaOH (2×25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was crystallized from isopropyl acetate

출처 및 근거

ORD 기록
ord-a8d1c264d5fa4c359d7ac1516dcb0bf2
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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