Diethyl Oxalate → Ethyl 2-(2-(tert-butoxycarbonylamino)-6-methoxyphenyl)-2-oxoacetate

HRID 425518Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.[Li]CCCC.[C:22](OCC)(=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[C:12]([O:11][C:10]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:16])([CH3:13])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 3-methoxyphenylcarbamate (25.6 g, 0.11 mol) in THF (300 mL) was added n-BuLi (0.25 mol, 1.6 M solution in pentane) at −78° C. The resulted solution was stirred at 0° C. for 3 hours and re-cooled to −78° C. followed by the addition of diethyl oxalate (20.1 g, 0.14 mol). The mixture was stirred at −78° C. for 45 min and at ambient temperature for one hour, and quenched with 1 N HCl. The mixture was extracted with ether. The organic solution was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography to give 3.70 g (27% based on recovered starting material) of the title compound: MS (ES+) m/z 324.3 (M+1).

Workup

temperaturere-cooled to −78° C.
stirringThe mixture was stirred at −78° C. for 45 min and at ambient temperature for one hour
customquenched with 1 N HCl
extractionThe mixture was extracted with ether
dry with materialThe organic solution was dried over sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo to dryness
customto give
custom3.70 g (27% based on recovered starting material) of the title compound

Sources & evidence

ORD record: ord-d02b4f1e69dd45cb870f259600216bfd
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106087B2

Reaction notes

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