Water → Ethyl 5-butoxy-1,3-oxazole-2-carboxylate
Reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([NH:7][CH2:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])=O)[CH3:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O.C(Cl)Cl>C(#N)C>[CH2:12]([O:11][C:9]1[O:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:16])=[N:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Butyl N-[ethoxy(oxo)acetyl]glycinate (783 g, 3.38 mol) was dissolved in 8 L of acetonitrile in a 50 L Chemglass reactor with overhead stirrer and P2O5 (415 g, 2.92 mol) was added in large portions, watching for exotherm. The reaction was heated to 60° C. for 1 hour and LCMS showed the reaction done. After cooling, water (8 L) was added at 20° C. and the reaction was transferred to a 50 L flask. Methylene chloride (8 L) was added, the layers split and the aqueous layer was extracted with three 2 L volumes of methylene chloride. The combined organic layers were washed with two 4 L portions of saturated aqueous NaHCO3, then dried with MgSO4 and evaporated to give an oil that was purified on silica eluting with 0-30% EtOAc/heptane to give the product as an oil.
Workup
- temperatureAfter cooling
- customthe reaction was transferred to a 50 L flask
- customthe layers split
- extractionthe aqueous layer was extracted with three 2 L volumes of methylene chloride
- washThe combined organic layers were washed with two 4 L portions of saturated aqueous NaHCO3
- dry with materialdried with MgSO4
- customevaporated
- customto give an oil that
- customwas purified on silica eluting with 0-30% EtOAc/heptane
Sources & evidence
- ORD record
- ord-3fd2f298d6214b4f97c385de6bd94e6d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598264B2
Reaction notes
Loading…