Phosphorus oxide (P4O10) → Methyl 3-(5-ethoxy-1,3-oxazol-2-yl)propanoate

HRID 2389909Notes

Reaction equation

O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([O:17][C:18](=[O:29])[CH2:19][NH:20][C:21](=O)[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH3:16]>C(#N)C.[Cl-].[Na+].O>[CH2:15]([O:17][C:18]1[O:29][C:21]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[N:20][CH:19]=1)[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of diphosphorus pentoxide (70.0 g, 433 mmol) in acetonitrile (200 mL) was added a solution of methyl 4-[(2-ethoxy-2-oxoethyl)amino]-4-oxobutanoate (20.0 g, 92.1 mmol) in acetonitrile (50 mL) at room temperature under an argon gas atmosphere. The mixture was stirred at 60° C. for 1 hr and poured into saturated brine (1.5 L), and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→30/70) to give the title compound (7.06 g, yield 38%).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→30/70)

Sources & evidence

ORD record: ord-f659b2c06c5043d1b171553cd7fd90fc
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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