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Sodium Hydroxide → 4-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(r,s)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylic acid

HRID 395009
ノート
印刷プレビュー

反応式

HRID 395009 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([F:36])[CH2:13][CH2:14][C:15]1([C:32]([O:34]C)=[O:33])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][S:23][C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[CH2:17][CH2:16]1)=[CH:9][C:8]([O:37][CH3:38])=[CH:7][CH:6]=2.[OH-].[Na+]>O1CCOCC1.CO>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]([F:36])[CH2:13][CH2:14][C:15]1([C:32]([OH:34])=[O:33])[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][S:23][C:24]3[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=3[F:31])[CH2:19][CH2:20]1)=[CH:9][C:8]([O:37][CH3:38])=[CH:7][CH:6]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 22468945Methyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(r,s)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylate

生成物 1

HCID 224689004-[3-(3-Chloro-6-methoxyquinolin-4-yl)-3-(r,s)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylic acid収率 58.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
70 °C

実験手順

A mixture of 0.07 g of methyl 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]piperidine-4-carboxylate in 3 cm3 of dioxane, 3 cm3 of methanol and 0.9 cm3 of aqueous 5N sodium hydroxide solution was maintained at a temperature in the region of 70° C. for 4 hours. After cooling to about 20° C., the reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue was chromatographed under atmospheric pressure, on a column of silica gel (particle size 70-200μ; mass 10 g), eluting with a dichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume). Fractions 10 to 15 were combined and then concentrated to dryness under the same conditions as above. 0.04 g of 4-[3-(3-chloro-6-methoxyquinolin-4-yl)-3-(R,S)-fluoropropyl]-1-[2-(2,5-difluorophenylthio)ethyl]-piperidine-4-carboxylic acid was obtained in the form of a white solid.

後処理

  1. temperatureAfter cooling to about 20° C.
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. customThe residue was chromatographed under atmospheric pressure, on a column of silica gel (particle size 70-200μ; mass 10 g)
  4. washeluting with a dichloromethane/methanol/aqueous ammonia mixture (40/5/0.5 by volume)
  5. concentrationconcentrated to dryness under the same conditions as above

出典と根拠

ORDレコード
ord-8394340726574c11a2f30091375963fe
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06603005B2

反応ノート

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