Phosphorus oxide (P4O10) → HCID 66801841, compound
Reaction equation
C([O:3][C:4](=O)[NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[F:16])C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O=P(Cl)(Cl)Cl>C(OC(=O)C)C>[F:16][C:9]1[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[C:13]2[C:8]=1[CH2:7][CH2:6][NH:5][C:4]2=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
[2-(2-Fluoro-5-methoxy-phenyl)-ethyl]carbamic acid ethyl ester (I-44c: 1.6 g, 0.006 mol) was reacted with P2O5 (1.87 g, 0.013 mol) and POCl3 (16 mL) and the resulting mixture was refluxed for 4 hrs at 100° C. The reaction was monitored by TLC (100% ethylacetate). The reaction mass was cooled to room temperature and concentrated under reduced pressure. The concentrate was quenched with ice-water and basified with 2N Na2CO3 solution to pH 8. The resulting solution was partitioned between ethyl acetate and water. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (2% methanol in DCM) afforded 0.3 g of the product (23.25% yield).
Workup
- temperatureThe reaction mass was cooled to room temperature
- concentrationconcentrated under reduced pressure
- customThe concentrate was quenched with ice-water and basified with 2N Na2CO3 solution to pH 8
- customThe resulting solution was partitioned between ethyl acetate and water
- washThe organic layer was washed with water, brine solution
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated
- customPurification by column chromatography on silica gel (2% methanol in DCM)
Sources & evidence
- ORD record
- ord-559c398856c247bd99e9eca93512a252
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946260B2
Reaction notes
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