Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5](Cl)=[O:6].[CH3:15][C:16]1[C:20]([CH2:21][N:22]2[CH2:26][CH2:25][C@@H:24]([NH:27][C:28](=[O:31])[CH2:29][NH2:30])[CH2:23]2)=[C:19]([CH3:32])[O:18][N:17]=1.CO>ClCCl.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([NH:30][CH2:29][C:28]([NH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([CH2:21][C:20]2[C:16]([CH3:15])=[N:17][O:18][C:19]=2[CH3:32])[CH2:23]1)=[O:31])=[O:6]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 3-fluoro-5-(trifluoromethyl)benzoyl chloride (0.058 mmol) in dichloromethane (1 mL) was added to a mixture of (R)-1-(3,5-dimethylisoxazol-4-ylmethyl)-3-(glycylamino)pyrrolidine (0.050 mmol) and piperidinomethylpolystyrene (58 mg) in chloroform (0.2 mL) and dichloromethane (0.75 mL). After the reaction mixture was stirred at room temperature for 2 h, methanol (1.0 mL) was added and the mixture was stirred at room temperature for 30 min. The reaction mixture was loaded onto Varian™ SCX column, and washed with CH3OH (16 mL). Product was eluted off using 2 N NH3 in CH3OH (6 mL) and concentrated to afford (R)-3-[N-(3-fluoro-5-(trifluoromethyl)benzoyl}glycyl]amino-1-(3,5-dimethylisoxazol-4-ylmethyl)pyrrolidine (Compound No. 1191) (19.5 mg, 88%): The purity was determined by RPLC/MS (100%); ESI/MS m/e 443.2 (M++H, C20H22F4N4O3).
Aufarbeitung
- stirringthe mixture was stirred at room temperature for 30 min
- washwashed with CH3OH (16 mL)
- washProduct was eluted off
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-54acb65eeef2441fb3d7c476ddbcff3e
- Quelldatensatz
- uspto-grants-2002_03
- Patentnummer
- US06362177B1
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