Hydrochloric Acid → HCID 59314067, compound

HRID 1402768Notes

Reaction equation

HRID 1402768 reaction equation
C([O:4][CH2:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Br:21])[CH:19]=2)[N:14]=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:12]1=[O:26])=[O:7])(=O)C.[Li+].[OH-].Cl>O1CCCC1.CO>[Br:21][C:18]1[CH:19]=[C:20]2[C:15]([N:14]=[C:13]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:12](=[O:26])[N:11]2[CH2:10][CH2:9][NH:8][C:6](=[O:7])[CH2:5][OH:4])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59314074HCID 59314074, compound

Product 1

HCID 59314067HCID 59314067, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(2-(7-Bromo-3-tert-butyl-2-oxoquinoxalin-1(2H)-yl)ethylamino)-2-oxoethyl acetate was dissolved in 4 mL of 1:1 tetrahydrofuran/methanol, and 0.99 mL of aq. 1N LiOH was added. After 30 minutes of stirring at room temperature the reaction was complete. Hydrochloric acid was used to adjust the pH to 6, and the solution was extracted with ethyl acetate 3 times, the combined organic layers washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to provide 197 mg of N-(2-(7-bromo-3-tert-butyl-2-oxoquinoxalin-1(2H)-yl)ethyl)-2-hydroxyacetamide. The product was pure by TLC and was used in the next step (Suzuki coupling) without purification.

Workup

  1. extractionthe solution was extracted with ethyl acetate 3 times
  2. washthe combined organic layers washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f4502c82ed94b28a443ea4abdc557dc
Source dataset
uspto-grants-2014_12
Patent number
US08912190B2

Reaction notes

Loading…