Trifluoroacetic acid → HCID 53357367, Verbindung

HRID 1807277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807277
[Cl:1][C:2]1[C:3]([F:47])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:46]=[CH:45][C:34]([CH2:35][CH2:36][NH:37]C(=O)OC(C)(C)C)=[CH:33][CH:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:37][CH2:36][CH2:35][C:34]1[CH:33]=[CH:32][C:31]([NH:30][C:28]([C@H:9]2[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[F:47])[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10]2)=[O:29])=[CH:46][CH:45]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 53357366HCID 53357366, Verbindung

Produkt 1

HCID 53357367HCID 53357367, VerbindungAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)phenethylcarbamate (77.3 mg, 0.113 mmol) in dichloromethane (3 ml) was treated with trifluoroacetic acid (2.23 g, 19.6 mmol) and stirred under argon. After 1.5 hrs, the reaction mixture was concentrated and the residue diluted with ethyl acetate, washed with saturated sodium carbonate, water and brine to give chiral (2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [4-(2-amino-ethyl)-phenyl]-amide (40.6 mg, 54.2%) as a white lyophilized solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue diluted with ethyl acetate
  3. washwashed with saturated sodium carbonate, water and brine

Quellen und Nachweise

ORD-Eintrag
ord-848b20bffe80402e8495590c24f9c290
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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