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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 909052
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
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Komponenten

4

Edukt 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

Produkt 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 acidAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5d74d013035143578b826a9c4b4eecb4
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08017607B2

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