Benzyloxycarbonylglycine → HCID 70043751, Verbindung

HRID 487421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 487421
[ClH:1].[C:2]([O:6][C:7](=[O:24])[CH2:8][N:9]1[CH2:14][CH2:13][NH:12][C@@H:11]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]1=[O:23])([CH3:5])([CH3:4])[CH3:3].C(OC([NH:35][CH2:36][C:37](O)=[O:38])=O)C1C=CC=CC=1.C(P(=O)(OCC)OCC)#N.Cl.O1CCOCC1>CO.[C].[Pd].C(N(CC)CC)C.CN(C)C=O>[ClH:1].[C:2]([O:6][C:7](=[O:24])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:37](=[O:38])[CH2:36][NH2:35])[C@@H:11]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]1=[O:23])([CH3:4])([CH3:3])[CH3:5]

Komponenten

9

Edukt 4

HCID 14349BenzyloxycarbonylglycineHCID 76257Diethyl cyanophosphonateHCID 204431481,4-Dioxane hydrochlorideHCID 70043966HCID 70043966, Verbindung

Produkt 1

HCID 70043751HCID 70043751, VerbindungAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 3.7 g of (S)-2-oxopiperazine-1,3-diacetic acid di-t-butyl ester hydrochloride, 3.3 g of N-benzyloxycarbonyl glycine and 10 ml of dimethylformamide were added dropwise, while stirring at 0° C., 3.1 g of diethyl cyanophosphonate then 3.2 g of triethylamine in the course of 10 minutes. The mixture was stirred for one hour at the same temperature then for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate and concentrated to give a crude product. The crude product was dissolved in 30 ml of methanol, to which were added 1 g of 10% palladium-carbon and 1.8 ml of 4N HCl-dioxane solution. The mixture was stirred for one hour at room temperature under hydrogen. The catalyst was removed, and the reaction mixture was concentrated under reduced pressure to afford 2.6 g of the title compound as a colorless oily product. This product was processed with ether to give colorless powder.

Aufarbeitung

  1. additionwere added dropwise
  2. customin the course of 10 minutes
  3. stirringThe mixture was stirred for one hour at the same temperature
  4. extractionwas subjected to extraction with ethyl acetate
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product
  8. stirringThe mixture was stirred for one hour at room temperature under hydrogen
  9. customThe catalyst was removed
  10. concentrationthe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-451a2812f81045bcaf4734c10b42413d
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294713

Notizen zur Reaktion

Wird geladen…