Diethylamine → (5-(N-Boc-N-2-picolylaminomethyl)pyrazine-2-carbonyl)-Ndelta-Cbz-L-ornithine

HRID 11851

Reaktionsgleichung

Reaktionsgleichung von HRID 11851
[C:1]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(NCC)C.CCN=C=NCCCN(C)C.Cl.[C:37]([N:44]([CH2:52][C:53]1[N:54]=[CH:55][C:56]([C:59](O)=[O:60])=[N:57][CH:58]=1)[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:37]([N:44]([CH2:52][C:53]1[N:54]=[CH:55][C:56]([C:59]([NH:16][C@H:15]([C:17]([OH:19])=[O:18])[CH2:14][CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])=[O:60])=[N:57][CH:58]=1)[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]

Komponenten

7

Edukt 4

HCID 8021DiethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7009570H-Orn(Z)-OHHCID 219736525-(N-Boc-N-2-picolylaminomethyl)pyrazine-2-carboxylic Acid

Produkt 1

HCID 86592263(5-(N-Boc-N-2-picolylaminomethyl)pyrazine-2-carbonyl)-Ndelta-Cbz-L-ornithine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

The compound obtained in Example 8-6 (160 mg) was dissolved in DMF (3.2 ml) and diethylamine (0.32 ml) was added. After one hour, the reaction solution was concebtrated and the residue obtained was dissolved in DMF (1 ml). Then, WSCI hydrochloride (73 mg), DMAP (31 mg), and a solution of the compound obtained in Example 13-3 in DMF (1 ml) were sequentially added. After 15 hours, the reaction solution was concentrated. After the addition of chloroform and 1 mol/l hydrochloric acid, the residue was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue was crude-purified by silica gel column chromatography (4 g, chloroform/ethyl acetate=1/2) to obtain the title compound (95.2 mg) as colorless syrup.

Aufarbeitung

  1. customthe residue obtained
  2. waitAfter 15 hours
  3. concentrationthe reaction solution was concentrated
  4. additionAfter the addition of chloroform and 1 mol/l hydrochloric acid
  5. extractionthe residue was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residue was crude-purified by silica gel column chromatography (4 g, chloroform/ethyl acetate=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-27b3171f15d74f3eb8897b1eb4d4be90
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098215B2

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