Ethylmorpholine → 1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine

HRID 378586

Reaktionsgleichung

Reaktionsgleichung von HRID 378586
C(N1CCOCC1)C.O.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.[C:31]([C@H:34]([C@@H:46]([CH2:55][CH:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1)[C:47]([N:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1)=[O:48])[CH2:35][N:36]1[C:40](=[O:41])[C:39]([CH3:43])([CH3:42])[N:38]([CH3:44])[C:37]1=[O:45])(O)=[O:32].Cl.[CH2:62]([O:69][NH2:70])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>C(Cl)Cl>[CH2:62]([O:69][NH:70][C:31]([C@H:34]([C@@H:46]([CH2:55][CH:56]1[CH2:57][CH2:58][CH2:59][CH2:60]1)[C:47]([N:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)=[O:48])[CH2:35][N:36]1[C:40](=[O:41])[C:39]([CH3:43])([CH3:42])[N:38]([CH3:44])[C:37]1=[O:45])=[O:32])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Komponenten

7

Edukt 5

HCID 7525Ethylmorpholine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 102312Benzyloxyamine hydrochlorideHCID 112701291-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperdineHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 543913361-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidineAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

0.74 g of N-ethylmorpholine, 0.60 g of hydroxybenzotriazole hydrate and 0.75 g of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide were added at 0° in succession to a solution of 1.38 g of 1-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine VI in 13 ml of methylene chloride and the mixture was stirred at 0° for 20 min. The reaction mixture was treated with 0.45 g of N-ethylmorpholine and 0.63 g of O-benzylhydroxylamine hydrochloride and stirred at 0° for 30 min. and at 22° for 17 hrs. The solution was diluted with 13 ml of methylene chloride, washed with sodium bicarbonate solution and dilute hydrochloric acid, dried and concentrated. The residue was crystallized from ethyl acetate/hexane and the crystallizate was dried, there being obtained 1.26 g (73%) of pure 1-[2(R)-[1(R)-(benzyloxycarbamoyl)-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperidine VII, m.p. 138-140°.

Aufarbeitung

  1. stirringstirred at 0° for 30 min. and at 22° for 17 hrs
  2. washwashed with sodium bicarbonate solution and dilute hydrochloric acid
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was crystallized from ethyl acetate/hexane
  6. customthe crystallizate was dried

Quellen und Nachweise

ORD-Eintrag
ord-b0f8dc542af5485b96430b617728d9b4
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06031103

Verknüpfte Notizen

Wird geladen…