Ethyl 3-bromo-2-oxobutanoate → HCID 68089378, compound

HRID 1615679Notes

Reaction equation

HRID 1615679 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.Br[CH:20]([CH3:28])[C:21](=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[CH3:28][C:20]1[N:3]2[C:2]([C:7]3[O:8][CH2:9][CH2:10][N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]=3[CH:5]=[CH:4]2)=[N:1][C:21]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 11117285Ethyl 3-bromo-2-oxobutanoateHCID 68089393HCID 68089393, compound

Product 1

HCID 68089378HCID 68089378, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-amino-2,3-dihydropyrido[3,4-b][1,4]oxazine-1-carboxylate (2.1 g, 8.37 mmol) in 100 mL of THF was added ethyl 3-bromo-2-oxobutanoate (3.482 g, 16.74 mmol). The mixture was stirred under reflux overnight. After removal of the solvent, the crude product was purified by silica gel column chromatography (EtOAc/PE v/v 2:1) to give 10-tert-butyl 4-ethyl 5-methyl-13-oxa-3,6,10-triazatricyclo[7.4.0.0{2,6}]trideca-1(9),2,4,7-tetraene-4,10-dicarboxylate (757 mg, 25% yield).

Workup

  1. temperatureunder reflux overnight
  2. customAfter removal of the solvent
  3. customthe crude product was purified by silica gel column chromatography (EtOAc/PE v/v 2:1)

Sources & evidence

ORD record
ord-31b4a932bada45ae94cdc5fbfa8054de
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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