2-Amino-5-chlorobenzoic acid → (R)-1-(4-chlorobenzyl)-3-[[N-(2-amino-5-chlorobenzoyl)glycyl]amino]pyrrolidine

HRID 133558

Reaktionsgleichung

Reaktionsgleichung von HRID 133558
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N=C=NC(C)C)(C)C.[Cl:21][C:22]1[CH:38]=[CH:37][C:25]([CH2:26][N:27]2[CH2:31][CH2:30][C@@H:29]([NH:32][C:33](=[O:36])[CH2:34][NH2:35])[CH2:28]2)=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[Cl:21][C:22]1[CH:38]=[CH:37][C:25]([CH2:26][N:27]2[CH2:31][CH2:30][C@@H:29]([NH:32][C:33](=[O:36])[CH2:34][NH:35][C:4](=[O:6])[C:3]3[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:2]=3[NH2:1])[CH2:28]2)=[CH:24][CH:23]=1

Komponenten

5

Edukt 3

HCID 124762-Amino-5-chlorobenzoic acidHCID 12734DiisopropylcarbodiimideHCID 54551710(R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine

Produkt 1

HCID 44453533(R)-1-(4-chlorobenzyl)-3-[[N-(2-amino-5-chlorobenzoyl)glycyl]amino]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Amino-5-chlorobenzoic acid (0.060 mL) and diisopropylcarbodiimide (0.060 mol) were added to a chloroform (2 mL) solution of (R)-1-(4-chlorobenzyl)-3-(glycylamino)pyrrolidine (0.050 mmol). The resulting reaction solution was stirred at room temperature for 15 hours. The mixture solution was loaded onto a Varian™ SCX column and washed with methanol (15 mL). The obtained crude product was eluted with a solution of 2 M NH3 in methanol (5 mL) and concentrated to thereby afford (R)-1-(4-chlorobenzyl)-3-[N-[2-amino-5-chlorobenzoyl]glycyl]amino]pyrrolidine (Compd. No. 1084) (12.7 mg, 60%). The purity was determined by RPLC/MS (87%). ESI/MS m/e 421.0 (M++H, C20H22Cl2N4O2).

Aufarbeitung

  1. customThe resulting reaction solution
  2. washwashed with methanol (15 mL)
  3. customThe obtained crude product
  4. washwas eluted with a solution of 2 M NH3 in methanol (5 mL)
  5. concentrationconcentrated to thereby afford (R)-1-(4-chlorobenzyl)-3-[N-[2-amino-5-chlorobenzoyl]glycyl]amino]pyrrolidine (Compd. No

Quellen und Nachweise

ORD-Eintrag
ord-051527a456854e87ace95143e4d333ed
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390830B1

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