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Citric Acid → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515734
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HRID 515734 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH:31]([CH3:33])[CH3:32])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([O:23]CC)=[O:22])[C:12]3=[CH:11][C:10]=2[C:9]=1[CH3:26])#[N:2].[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:29]=1[O:30][CH:31]([CH3:33])[CH3:32])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]3=[CH:11][C:10]=2[C:9]=1[CH3:26])#[N:2]
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 67248141Ethyl 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

생성물 1

HCID 583295982-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid수율 90.3%

시약·촉매·용매 1

HCID 31275
1,4-Dioxane
용매

실험 절차

To a solution of ethyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (130 mg, 0.291 mmol) in dioxane (2 mL) was added a 1 M LiOH aqueous solution (1.747 mL, 1.747 mmol). The reaction mixture was stirred at room temperature for 5 h, acidified to pH 3 with 0.5 M citric acid aqueous solution, and extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated to give the title compound as pink solid (110 mg). LCMS m/z=419.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (d, J=6.0 Hz, 6H), 2.25-2.35 (m, 1H), 2.41 (s, 3H), 2.67 (dd, J=16.5, 8.5 Hz, 1H), 2.88-2.98 (m, 2H), 3.73-3.81 (m, 1H), 3.97-4.04 (m, 1H), 4.10-4.16 (m, 1H), 4.62-4.68 (m, 1H), 4.97 (s, 2H), 6.17 (s, 1H), 6.84 (d, J=8.7 Hz, 1H), 6.97 (d, J=8.7 Hz, 1H), 7.01 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.6, 2.2 Hz, 1H), 7.63 (d, J=2.2 Hz, 1H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a9c1d0178f1a4480a801c05b42eba2a4
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108969B2

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