Dicyclohexylcarbodiimide → (R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamate

HRID 22386

Reaktionsgleichung

Reaktionsgleichung von HRID 22386
[C:1]([NH:11][C@@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH2:17][N:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:5]1([CH2:4][O:3][C:1](=[O:2])[NH:11][C@H:12]([CH3:13])[C:14](=[O:16])[NH:17][N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 70832N-Cbz-d-alanineHCID 1365891-Aminopyrrole

Produkt 1

HCID 131718294(R)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution consisting of carbobenzyloxy-D-alanine (10.0 g) and N-aminopyrrole (3.68 g) in dry DCM (224 ml) was added DCC (9.71 g) at 0° C. under nitrogen. The cooling bath was removed after ten minutes and the reaction mixture was allowed to stir at room temperature for 24 hours. The suspension was filtered and the DCU filter cake was washed with hot ethyl acetate. Concentration of the filtrate gave the crude product. Recrystallization from EtOAc/hexane afforded 11.69 g of the desired product as a solid, m.p. 172°-174° C.

Aufarbeitung

  1. customThe cooling bath was removed after ten minutes
  2. filtrationThe suspension was filtered
  3. filtrationthe DCU filter cake
  4. washwas washed with hot ethyl acetate
  5. customConcentration of the filtrate gave the crude product
  6. customRecrystallization from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2b203e932a2844f291e5a3f318da299c
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428053

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