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Diisopropylethylamine → 3-{2-Ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenyl}-propionic acid

HRID 2240817
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인쇄 미리보기

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HRID 2240817 반응식
[CH2:1]([C:3]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11](=[O:24])[C:12]2[S:13][C:14]([CH3:23])=[C:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]=23)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH:26]=[CH:27][C:28]([OH:30])=[O:29])[CH3:2].CCN(C(C)C)C(C)C>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11](=[O:24])[C:12]2[S:13][C:14]([CH3:23])=[C:15]3[CH2:20][C:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][C:16]=23)[CH:6]=[C:5]([CH3:25])[C:4]=1[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH3:2]
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참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 671896023-{2-Ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propenyl]-phenyl}-acrylic acid

생성물 1

HCID 167379863-{2-Ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenyl}-propionic acid수율 44.8%

시약·촉매·용매 2

HCID 23938Palladium촉매2회
HCID 702
Ethanol
용매

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온도
50 °C

실험 절차

To a solution of 3-{2-ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propenyl]-phenyl}-acrylic acid (340 mg, 0.805 mmol) and DIPEA (182 mg, 1.41 mmol) in ethanol, Pd/C (340 mg, 10% Pd, moistened with 50% water) is added and the resulting slurry is stirred at 50° C. for 72 h under 10 bar of H2. Another portion of Pd/C is added and stirring is continued for 16 h at 50° C. under 10 bar of H2. The reaction mixture is filtered and the filtrate is evaporated. The crude product is purified by prep. HPLC (Grom-Sil 120 ODS-4-HE, 30×75 mm, 10 μm, acetonitrile/water (0.5% HCOOH), 20% to 95% acetonitrile) to give 3-{2-ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenyl}-propionic acid (154 mg) as a colourless foam; LC-MS: tR=1.15 min, [M+1]=427.30.

후처리

  1. stirringstirring
  2. waitis continued for 16 h at 50° C. under 10 bar of H2
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated
  5. customThe crude product is purified by prep

출처 및 근거

ORD 기록
ord-d3ddc34af6934908a18ba664127c4c62
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723378B2

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