Reaktionsgleichung
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N=C=NC(C)C)(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:32][C:33]1[CH:50]=[CH:49][C:36]([CH2:37][N:38]2[CH2:42][CH2:41][CH:40]([CH2:43][NH:44][C:45](=[O:48])[CH2:46][NH2:47])[CH2:39]2)=[CH:35][CH:34]=1>C(Cl)(Cl)Cl.C(O)(C)(C)C>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH:47][CH2:46][C:45]([NH:44][CH2:43][CH:40]1[CH2:41][CH2:42][N:38]([CH2:37][C:36]2[CH:49]=[CH:50][C:33]([Cl:32])=[CH:34][CH:35]=2)[CH2:39]1)=[O:48])=[O:6]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
2-Amino-4,5-difluorobenzoic acid (0.060 mmol), diisopropylcarbodiimide (0.060 mmol) and HOBt (0.060 mmol) were added to a solution of 1-(4-chlorobenzyl)-3-[(glycylamino)methyl]pyrrolidine (0.050 mmol) in chloro form (1.35 mL) and tert-butanol (0.05 mL). The resulting reaction Mixture was stirred at room temperature for 19 hours, then loaded onto a Varian™ SCX column and washed with methanol/chloroform=1:1 (10 mL) and methanol (10 mL). The obtained crude product was eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby afford 3-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (Compd. No. 1506) (22.0 mg, quantitative). The purity was determined by RPLC/MS (92%). ESI/MS m/e 437 (M++H, C21H23ClF2N4O2).
Aufarbeitung
- customThe resulting reaction Mixture
- washwashed with methanol/chloroform=1:1 (10 mL) and methanol (10 mL)
- customThe obtained crude product
- washwas eluted with a 2 M methanol solution of NH3 (5 mL)
- concentrationconcentrated to thereby afford 3-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(4-chlorobenzyl)pyrrolidine (Compd. No
Quellen und Nachweise
- ORD-Eintrag
- ord-9f61871088e5409c860111d2ce601a79
- Quelldatensatz
- uspto-grants-2008_06
- Patentnummer
- US07390830B1
Verknüpfte Notizen
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