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

HRID 22380

Reaktionsgleichung

Reaktionsgleichung von HRID 22380
[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 1365891-AminopyrroleHCID 736104N-carbobenzyloxyalanine

Produkt 1

HCID 15838188(S)-phenylmethyl-[1-methyl-2-oxo-2-(1H-pyrrol-1-ylamino)ethyl]carbamateAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of carbobenzyloxy-L-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 17 hours. The mixture was filtered and the solid DCU filter cake was washed with hot ethyl acetate. Concentration of the combined filtrate gave the crude product. Recrystallization from ethyl acetate/hexane afforded 10.46 g of the product as a solid, m.p. 169°-171° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-db24663bf31b482a858d169325ba9915
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428053

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