Diethyl Ether → 3-(4-tert-Butyl-2-nitro-phenyl)-2-oxo-propionic Acid Ethyl Ester

HRID 23494Notes

Reaction equation

HRID 23494 reaction equation
[K].CCOCC.[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[C:8]([O:10]CC)=O.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>CCO>[CH2:15]([O:14][C:7](=[O:13])[C:8](=[O:10])[CH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:17]([CH3:20])([CH3:18])[CH3:19])=[CH:22][C:23]=1[N+:28]([O-:30])=[O:29])[CH3:16]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 5462222PotassiumHCID 109544154-Tert-butyl-1-methyl-2-nitrobenzene

Product 1

HCID 542454313-(4-tert-Butyl-2-nitro-phenyl)-2-oxo-propionic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by adapting the procedure described by Gagliardi S., et al., in J. Med. Chem., 1998;41:1568 using potassium (1.66 g, 42.4 mmol), Et2O (200 mL), EtOH (10 mL), diethyl oxalate (7.56 g, 51.8 mmol), and 4-tert-butyl-1-methyl-2-nitrobenzene (prepared in Example WW; 10.0 g, 51.8 mmol). MS(APCI): 294 (M+H).

Sources & evidence

ORD record
ord-1598bca282c84c3d8e0b6d204eb7688d
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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