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3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester → 3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid

HRID 2240820
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HRID 2240820 반응식
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([C:29]([F:32])([F:31])[F:30])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:33][CH3:34])C>C1COCC1.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:28][C:25]1([CH3:27])[CH2:24][CH2:23][C:22]2=[C:18]([C:16](=[O:17])[CH2:15][CH2:14][C:10]3[CH:11]=[C:12]([CH3:13])[C:7]([CH2:6][CH2:5][C:4]([OH:35])=[O:3])=[C:8]([CH2:33][CH3:34])[CH:9]=3)[S:19][C:20]([C:29]([F:32])([F:30])[F:31])=[C:21]2[CH2:26]1
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참가 물질

6

반응물 1

HCID 575089143-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester

생성물 1

HCID 167354333-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid수율 64.2%

시약·촉매·용매 4

HCID 311Citric Acid용매HCID 887Methanol용매
HCID 3939
Lithium Hydroxide
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester (340 mg, 0.668 mmol) in THF (5 mL), methanol (4 mL) and 2 N aq. LiOH (2 mL) is stirred at rt for 2 h before it is diluted with 10% aq. citric acid solution and extracted with DCM (3×75 mL). The combined organic extracts are dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified on prep. TLC plates with heptane:EA 3:4 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid (206 mg) as a colourless glass; LC-MS: tR=1.17 min, [M+1]=481.36.

후처리

  1. extractionextracted with DCM (3×75 mL)
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent of the filtrate is evaporated
  5. customThe crude product is purified on prep

출처 및 근거

ORD 기록
ord-f22d479d39d84d69b58c49100ad4f434
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723378B2

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