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Hydrochloric Acid → rac-4-{[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]amino}-benzoic acid

HRID 909060
ノート
印刷プレビュー

反応式

HRID 909060 の反応式
C([O:3][C:4](=[O:42])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:18][C@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=3[F:26])[C@:16]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=3[F:36])([C:27]#[N:28])[C@@H:15]2[CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:13])=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>CO>[Cl:25][C:21]1[C:20]([F:26])=[C:19]([C@H:17]2[CH2:18][N:14]([C:12]([NH:11][C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:42])=[O:3])=[CH:10][CH:9]=3)=[O:13])[C@@H:15]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C@@:16]2([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[F:36])[C:27]#[N:28])[CH:24]=[CH:23][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 51355586rac-4-{[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid ethyl ester

生成物 1

HCID 51355587rac-4-{[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]amino}-benzoic acid収率 53.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of rac-4-{[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid ethyl ester (0.2 g, 0.32 mmol) in methanol (5 mL) was added an aqueous solution (1 N) of NaOH (5 mL, 5 mmol). The reaction mixture was stirred at room temperature for 20 h. The “pH” of the mixture was adjusted to 5-6 by diluted aqueous HCl solution. The mixture was partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (75% EtOAc in hexanes) to give rac-4-{[(2S,3R,4S)-4-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-2-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]amino}-benzoic acid as a white solid (0.1 g, 50%). HRMS (ES+) m/z Calcd for C30H27Cl2F2N3O3+H [(M+H): 586.1471; Found: 586.1473.

後処理

  1. customThe mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (75% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-478b1dbf1bf04d05b2222a6fed7839eb
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…

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