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Trifluoroacetic acid → rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid

HRID 909052
ノート
印刷プレビュー

反応式

HRID 909052 の反応式
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=2[F:20])[C@:10]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[F:30])([C:21]#[N:22])[C@@H:9]1[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:19][C:15]1[C:14]([F:20])=[C:13]([C@H:11]2[CH2:12][N:8]([CH2:7][C:6]([OH:36])=[O:5])[C@@H:9]([CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C@@:10]2([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[F:30])[C:21]#[N:22])[CH:18]=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 51355302rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid tert-butyl ester

生成物 1

HCID 51355303rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid収率 85.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid tert-butyl ester (2.1 g, 3.9 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 24 h. The mixture was concentrated, and water was added. The “pH” of the mixture was adjusted to 6-7 by saturated aqueous NaHCO3 solution, then extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried over MgSO4, then concentrated to give rac-[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidin-1-yl]-acetic acid as a off-white solid (1.6 g, 85%). HRMS (ES+) m/z Calcd for C24H24Cl2F2N2O2+H [(M+H): 481.1256; Found: 481.1254.

後処理

  1. concentrationThe mixture was concentrated
  2. additionwater was added
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-5d74d013035143578b826a9c4b4eecb4
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017607B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート