Benzylamine → (S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1970648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970648
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C.C(Cl)CCl>[CH2:12]([O:11][C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3](=[O:5])[NH:45][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 181649HOAt

Produkt 1

HCID 690250(S)-2-Benzylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5.00 g Z-Pro-OH in 50 ml DMF were added 3.84 g EDC, 2.73 g HOAt, 7.3 ml DIPEA and 2.2 ml benzylamine at 0° C. After stirring for 2 h the reaction mixture was concentrated, the residue was dissolved in dichloromethane and subsequently extracted with aqueous LiCl (4%), 0.1 M HCl and saturated NaHCO3. The crude product obtained after evaporation of the solvent was pure enough for the subsequent transformation.

Aufarbeitung

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionsubsequently extracted with aqueous LiCl (4%), 0.1 M HCl and saturated NaHCO3

Quellen und Nachweise

ORD-Eintrag
ord-7becf474359741b6ba44c6bf607b4554
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426420B2

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