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Lithium hydroxide, monohydrate → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid

HRID 546200
ノート
印刷プレビュー

反応式

HRID 546200 の反応式
C[O:2][C:3](=[O:24])[C@@H:4]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([Cl:23])[CH:14]=1)[CH2:5][C@H:6]1[CH2:10][CH2:9][C:8]([F:12])([F:11])[CH2:7]1.O.[OH-].[Li+]>C(O)C.O>[Cl:23][C:15]1[CH:14]=[C:13]([CH:4]([CH2:5][C@H:6]2[CH2:10][CH2:9][C:8]([F:12])([F:11])[CH2:7]2)[C:3]([OH:24])=[O:2])[CH:18]=[CH:17][C:16]=1[S:19]([CH3:22])(=[O:20])=[O:21]
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 168937Lithium hydroxide, monohydrateHCID 67189626(R)-2-(3-Chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid methyl ester

生成物 1

HCID 671892282-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid収率 86%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water
溶媒

反応条件

温度
25 °C

実験手順

(R)-2-(3-Chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid methyl ester (294 mg, 0.77 mmol) was dissolved in ethanol (8 mL) and treated with a solution of lithium hydroxide monohydrate (81 mg, 1.9 mmol) in water (2 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC (˜1 hr). The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((R)-3,3-difluoro-cyclopentyl)-propionic acid (242 mg, 86%) as a mixture of two diastereomers as a light yellow foam: ES-HRMS m/e calcd for C15H17O4SClF2 (M+Na)+ 389.0396, observed 389.0394; 1H NMR (300 MHz, CDCl3) δ 1.06-2.38 (m, 9H, CH and 4×CH2), 3.28 (s, 3H, SO2CH3), 3.65 (m, 1H, ArCH), 7.42 (m, 1H, Ar), 7.54 (m, 1H, Ar), 8.14 (m, 1H, Ar).

後処理

  1. customall consumed by TLC (˜1 hr)
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto remove the ethanol
  4. extractionThis was then extracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6032137fa0af466da28402118ad7b817
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935699B2

反応ノート

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