Hydrochloric Acid → 2-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetic Acid

HRID 515677ノート

反応式

HRID 515677 の反応式
[CH:1]1([C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]4[N:19]5[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26]CC)=[O:25])[C:18]5=[N:17][C:16]=4[CH:29]=3)=[CH:8][C:7]=2[C:32]([F:35])([F:34])[F:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl>O1CCOCC1>[CH:1]1([C:6]2[CH:31]=[CH:30][C:9]([CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]4[N:19]5[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([OH:26])=[O:25])[C:18]5=[N:17][C:16]=4[CH:29]=3)=[CH:8][C:7]=2[C:32]([F:34])([F:35])[F:33])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67248467Ethyl 2-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate

生成物 1

HCID 583295932-(6-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetic Acid収率 100.3%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Ethyl 2-(6-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl)acetate (0.109 g, 0.224 mmol) was dissolved in dioxane (2.5 mL) and 1.0 M aqueous lithium hydroxide (0.672 mL, 0.672 mmol) was added. The reaction mixture was stirred at room temperature for 1.5 h and then acidified (pH 2) with 1.0 M HCl. The reaction mixture was extracted three times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (103 mg). LCMS m/z=459.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.65 (m, 2H), 1.67-1.79 (m, 2H), 1.80-1.91 (m, 2H), 2.05-2.14 (m, 2H), 2.42-2.53 (m, 1H), 2.89 (d, J=7.1 Hz, 1H), 2.95-3.22 (m, 2H), 3.33-3.43 (m, 1H), 3.78-3.87 (m, 1H), 4.03-4.12 (m, 1H), 4.14-4.23 (m, 1H), 5.09 (s, 2H), 6.88 (d, J=2.4 Hz, 1H), 6.97 (dd, J=8.8, 2.5 Hz, 1H), 7.48 (d, J=8.2 Hz, 1H), 7.57 (d, J=8.1 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.68 (s, 1H).

後処理

  1. extractionThe reaction mixture was extracted three times with EtOAc
  2. dry with materialthe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6727251fe1cd4cdd93cd689b577ee07b
出典データセット
uspto-grants-2015_08
特許番号
US09108969B2

反応ノート

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