Hydrochloric Acid → tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate

온도

0 °C

To a 150 mL RBF containing (R)—N-((1S,2R)-1-fluoro-1-phenylbut-3-en-2-yl)-2-methylpropane-2-sulfinamide (107.00 mg, 397 μmol) was added methanol (5 mL) and the mixture was allowed to stir at 0° C. for 10 min. At this time, HCl (4N) (993 μl, 3972 μmol) was added and the reaction was allowed to stir for 30 min. Then TEA (1384 μl, 9930 μmol) was added to the mixture followed by DCM (2 ml) and BOC2O (173 mg, 794 μmol) in one portion. The reaction was allowed to stir overnight and then the bulk of the methanol was removed by evaporation. The residue was dissolved in EtOAc and washed with HCL (0.5 N, 2×40 ml). The combined aqueous layers were back extacted with EtOAc. The combined organics were washed with sodium bicarbonate (1×50 ml, sat) and brine and then dried with sodium sulfate. The dried solution was passed though a plug of silica gel to give tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate (111.0 mg). Rf=0.45 in 20% EtOAc in hexanes, UV active and stain yellow to anisaldehyde. LC/MS give an ionization for eliminated product (mass=190).

1. stirringto stir for 30 min
2. stirringto stir overnight
3. customthe bulk of the methanol was removed by evaporation
4. dissolutionThe residue was dissolved in EtOAc
5. washwashed with HCL (0.5 N, 2×40 ml)
6. washThe combined organics were washed with sodium bicarbonate (1×50 ml, sat) and brine
7. dry with materialdried with sodium sulfate

ORD 기록

ord-6899459cf902437c8392b3309450d95b

출처 데이터셋

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08163909B2