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Lithium Hydroxide → 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid

HRID 2040559
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HRID 2040559 반응식
[CH:1]1([CH2:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[NH:19][C:18]5[CH:23]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:24][CH2:25][C:17]=5[C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:34]([F:37])([F:36])[F:35])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>O1CCOCC1>[CH:1]1([CH2:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][O:13][C:14]3[CH:22]=[CH:21][C:20]4[NH:19][C:18]5[CH:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][CH2:25][C:17]=5[C:16]=4[CH:15]=3)=[CH:10][C:9]=2[C:34]([F:37])([F:35])[F:36])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 67211498Ethyl 2-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

생성물 1

HCID 446242702-(7-(4-(Cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid수율 51.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of ethyl 2-(7-(4-(cyclohexylmethyl)-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (40 mg, 0.078 mmol) in dioxane was added 1 M LiOH aqueous solution (0.39 mL, 0.39 mmol). The reaction mixture was stirred at room temperature for 5 h. The solvent was partly removed, then diluted with water, acidified with HCl solution. The pinkish solid was collect and dried to give the title compound (19.5 mg). LCMS m/z=486.3 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 0.96-1.06 (m, 2H), 1.14-1.22 (m, 3H), 1.55-1.70 (m, 6H), 2.05-2.10 (m, 1H), 2.40 (dd, J=16.0 and 9.0 Hz, 1H), 2.62-2.75 (m, 6H), 3.42-3.50 (m, 1H), 5.12 (s, 2H), 6.72 (dd, J=8.7 and 2.4 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 7.21 (d, J=8.8 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.66 (d, J=7.8 Hz, 1H), 7.75 (s, 1H), 10.48 (s, 1H), 12.20 (br, 1H).

후처리

  1. customThe solvent was partly removed
  2. additiondiluted with water
  3. customThe pinkish solid was collect
  4. customdried

출처 및 근거

ORD 기록
ord-2220d4332bb94e6388366cb2078ade20
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08580841B2

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