Sodium Hydroxide → HCID 18435619, compound

HRID 2304456Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([NH:9][OH:10])=[O:8])[CH2:3][CH:4](C)C.[CH:11](=O)[CH2:12][CH2:13][C:14](=O)[CH2:15][CH3:16].[OH-].[Na+].[CH3:21]O.O>>[CH:3]([C:2]1[C:7](=[O:8])[N:9]([OH:10])[C:14]([CH2:15][CH3:16])=[C:13]([CH2:12][CH3:11])[N:1]=1)([CH3:4])[CH3:21]

Participants

Reactant 4

HCID 14798Sodium Hydroxide

HCID 3080766Leucine hydroxamate

HCID 53236054-oxohexanal

HCID 22242641Methanol--water (1/1)

Product 1

HCID 18435619HCID 18435619, compound

Conditions

Temperature: -30 °C

Procedure

3-isopropyl-5,6diethyl-1-hydroxy-2-oxo-1,2dihydropyrazine is prepared by dissolving leucine hydroxamic acid (73 mg) in a mixture of methanol/water (1/1) (5 mL) and cooling to −30° C. and mixing with 1,4-hexanedione (57 mg) at −30° C. To this mixture, a very dilute solution of (˜0.5M NaOH) is added to maintain the pH above 7.0 but not greater than 8.5 for about one hour. The temperature is then slowly brought to room temperature, and the mixture is stirred at room temperature overnight. The solid that is formed is filtered and recrystallized from ethanol/water mixture. Yield 25 mg.

Workup

temperatureto maintain the pH above 7.0
customis then slowly brought to room temperature
customThe solid that is formed
filtrationis filtered
customrecrystallized from ethanol/water mixture

Sources & evidence

ORD record: ord-21b6de23804949ea81b7701c3432e35b
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06436933B1

Reaction notes

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