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

HRID 2040549

反応式

HRID 2040549 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[CH:17]([CH2:20][C:21]([O:23]CC)=[O:22])[CH2:18][CH2:19][C:11]=3[C:10]=2[CH:9]=1)#[N:2].[Li+].[OH-]>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[CH:17]([CH2:20][C:21]([OH:23])=[O:22])[CH2:18][CH2:19][C:11]=3[C:10]=2[CH:9]=1)#[N:2]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67211600Ethyl 2-(7-(3-Cyano-4-cyclohexylbenzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

生成物 1

HCID 446241412-(7-(3-Cyano-4-cyclohexylbenzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic Acid収率 56.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of ethyl 2-(7-(3-cyano-4-cyclohexylbenzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (185.3 mg, 0.406 mmol) in 1,4-dioxane (5.0 mL) was added 1 M aqueous LiOH solution (1.22 mL, 1.22 mmol). The mixture was stirred at room temperature for 5 h. The mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then acidified with 1 N aqueous HCl acid solution to pH 4. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was triturated with dichloromethane to provide the title compound as a pink solid (98.9 mg). LCMS m/z=429.6 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.31 (m, 1H), 1.33-1.54 (m, 4H), 1.68-1.74 (m, 1H), 1.74-1.88 (m, 4H), 2.08 (dd, J=4.93, 3.54 Hz, 1H), 2.34 (dd, J=16.04, 8.97 Hz, 1H), 2.61-2.76 (m, 4H), 2.81-2.89 (m, 1H), 3.45 (bs, 1H), 5.07 (s, 2H), 6.70 (dd, J=8.78, 2.46 Hz, 1H), 6.91 (d, J=2.40 Hz, 1H), 7.19 (d, J=8.72 Hz, 1H), 7.52 (d, J=8.08 Hz, 1H), 7.72 (dd, J=8.15, 1.71 Hz, 1H), 7.81 (d, J=1.52 Hz, 1H), 10.46 (s, 1H), 12.18 (bs, 1H).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was triturated with dichloromethane

出典と根拠

ORDレコード
ord-89f7ecc479dc49e7b6c575ce71af566a
出典データセット
uspto-grants-2013_11
特許番号
US08580841B2

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