Leucine, N-carboxy-, N-benzyl ester, L- → N2-[(benzyloxy)carbonyl)-N1-[(3S)-2-oxotetrahydrofuran-3-yl]-L-leucinamide

HRID 131097

Reaktionsgleichung

Reaktionsgleichung von HRID 131097
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Br.[NH2:21][C@H:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24].C1C=CC2N(O)N=NC=2C=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH2:4]([O:3][C:1]([NH:11][C@H:12]([C:17]([NH:21][C@H:22]1[CH2:27][CH2:26][O:25][C:23]1=[O:24])=[O:19])[CH2:13][CH:14]([CH3:15])[CH3:16])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

8

Edukt 5

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 162131383S-3-Aminodihydrofuran-2(3H)-one hydrobromide

Produkt 1

HCID 22859269N2-[(benzyloxy)carbonyl)-N1-[(3S)-2-oxotetrahydrofuran-3-yl]-L-leucinamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 22728543Water ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

3.51 g (13.25 mmol) of Cbz-L-Leucine, 2.41 g (1 eq.) of (S)-2-amino-4-butyrolactone hydrobromide, 1.97 g of HOBT (1.1 eq.) and 5.59 g (2.2 eq.) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) is dissolved in 60 ml of anhydrous DMF then 7.64 ml (3.3 eq.) of N,N-diisopropylethylamine is added. The reaction mixture is stirred for 15 hours at 20° C. before being poured into 200 ml of a 1/1 mixture of ethyl acetate/water. After stirring and decantation, the organic solution is washed successively with 100 ml of a saturated solution of NaHCO3, 50 ml of water, 100 ml of a 1M solution of citric acid and finally 100 ml of a solution of salt water. The organic phase is dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The oil obtained is washed using isopentane and then crystallized from a dichloromethane/isopentane mixture. A white solid is obtained with a yield of 68%. Melting point: 130-131° C.

Aufarbeitung

  1. stirringAfter stirring
  2. washdecantation, the organic solution is washed successively with 100 ml of a saturated solution of NaHCO3, 50 ml of water, 100 ml of a 1M solution of citric acid and finally 100 ml of a solution of salt water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under vacuum
  6. customThe oil obtained
  7. washis washed
  8. customcrystallized from a dichloromethane/isopentane mixture
  9. customA white solid is obtained with a yield of 68%

Quellen und Nachweise

ORD-Eintrag
ord-106b5825f2804658830e02e10ee85872
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384933B2

Verknüpfte Notizen

Wird geladen…