Potassium Hydroxide → 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

HRID 1713945ノート

反応式

HRID 1713945 の反応式
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C)=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO.C1COCC1.O.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][C:21]([N:23]([CH3:25])[CH3:24])=[O:22])[C:8]=2[C:26]2[O:30][CH:29]=[N:28][CH:27]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 68437594methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate

生成物 1

HCID 114635753-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylic acid

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To a solution of methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-(1,3-oxazol-5-yl)-1H-indole-6-carboxylate (from Step 5) in MeOH/THF/H2O (0.05 M, 1:1:1, v:v:v) was added KOH (5 eq.). The resulting solution was stirred at RT overnight. The reaction mixture was diluted with EtOAc, then washed with hydrochloric acid (1N), brine, and dried over Na2SO4. Evaporation gave an off-white foam, which was purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min) to give the title compound as a white powder after lyophilization (53%).

後処理

  1. washwashed with hydrochloric acid (1N), brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation
  4. customgave an off-white foam, which
  5. customwas purified by RP-HPLC (column: Waters X-terra C18, 19×150 mm, 5 micron; flow 20 mL/min)

出典と根拠

ORDレコード
ord-5488244d0d874fe68b68748858dc9334
出典データセット
uspto-grants-2010_09
特許番号
US07795250B2

反応ノート

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