Lithium hydroxide, monohydrate → 4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

HRID 1080766ノート

反応式

HRID 1080766 の反応式
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+]>CO.O1CCCC1.O>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[CH:14]=[C:13]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 11453373Methyl 4-((5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

生成物 1

HCID 112931194-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid収率 88%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of methyl 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoate (0.25 g.) in methanol (5 ml.) and tetrahydrofuran (4 ml.), under an atmosphere of nitrogen, was treated with a solution of lithium hydroxide monohydrate (0.12 g.) in water (2 ml.). The mixture was stirred for 20 hours and then concentrated to remove tetrahydrofuran. The resulting aqueous solution was acidified with 1M hydrochloric acid (20 ml.). The white precipitate which formed was separated by filtration, washed with a little water, and recrystallized from a mixture of toluene and hexane to give the title compound (0.212 g., 88%) as an off-white powder; m.p. 157°-158° C.

後処理

  1. concentrationconcentrated
  2. customto remove tetrahydrofuran
  3. customThe white precipitate which formed
  4. customwas separated by filtration
  5. washwashed with a little water
  6. customrecrystallized from a mixture of toluene and hexane

出典と根拠

ORDレコード
ord-99abb6846c614f058f0c29ebba19532e
出典データセット
uspto-grants-1996_12
特許番号
US05583152

反応ノート

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