Propylene Oxide → alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic Acid

HRID 892411

Reaktionsgleichung

Reaktionsgleichung von HRID 892411
BrCC1C(CBr)=NC2C(=CC=CC=2)N=1.C([O:17][C:18](=[O:37])[CH:19]([NH2:36])[CH2:20][C:21]1[C:30]([CH2:31][P:32]([OH:35])([OH:34])=[O:33])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)C.[OH-].[K+].C1OC1C>O>[NH2:36][CH:19]([CH2:20][C:21]1[C:30]([CH2:31][P:32]([OH:34])([OH:35])=[O:33])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1)[C:18]([OH:37])=[O:17]

Komponenten

6

Edukt 4

HCID 6378Propylene OxideHCID 14797Potassium HydroxideHCID 184492,3-Bis(bromomethyl)quinoxalineHCID 10315115alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid ethyl ester

Produkt 1

HCID 10470686alpha-Amino-3-(phosphonomethyl)-2-quinoxalinepropanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

The crude hydrobromide of α-amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid ethyl ester (1.4 mmole, 600 mg) was added to 1N aqueous potassium hydroxide (5.75 mL). The mixture was stirred overnight at room temperature, and then applied to an ion-exchange column (20 mL volume, Amberlite IRA 400) which had been prewashed with deionized water (40 mL). The column was washed to neutrality with deionized water, and the elution was continued with 0.5N hydrochloric acid. The acidic eluate was evaporated to dryness under reduced pressure, the residue was stripped with water (2×30 mL), benzene (2×30 mL), and dissolved in ethanol (10 mL). This solution was treated with propylene oxide (14.5 mmole, 1 mL), stirred for 30 minutes, the precipitate was collected by filtration, washed successively with cold ethanol and diethyl ether, and dried in vacuo at 85° C. The α-amino-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (300 mg) melted at 176° C. with decomposition; MS (pos. FAB) 312 (MH+ ); 1H NMR (D2O, 400 MHz): δ3.29 (dd, J1 =21 Hz, J2 =6 Hz, 2H, CH2 --P), 3.69 (m, 2H, CH2), 4.41 (m, 1H, CH), 7.56 (m, 2H, ArH), 7.71 and 7.81 (m, 2H, ArH).

Aufarbeitung

  1. washThe column was washed to neutrality with deionized water
  2. washthe elution
  3. customThe acidic eluate was evaporated to dryness under reduced pressure
  4. dissolutiondissolved in ethanol (10 mL)
  5. stirringstirred for 30 minutes
  6. filtrationthe precipitate was collected by filtration
  7. washwashed successively with cold ethanol and diethyl ether
  8. customdried in vacuo at 85° C

Quellen und Nachweise

ORD-Eintrag
ord-d3e5ef38cb3d422abd5acba1c0326f5c
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118675

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