Methyl Acetate → HCID 67957564, compound

Temperature

-78 °C

Add LDA (2M in heptane/THF, 3.4 mL, 6.9 mmol) to a solution of methyl acetate (0.6 mL, 6.9 mmol) in THF (5 mL) dropwise via a syringe at −78° C. After stirring at −78° C. for 30 min, add a solution of CITi(Oi-Pr)3 (1.8 mL, 7.6 mmol) in THF (5 mL) dropwise. After stirring for another 30 min, add (R)—N-(1-(3-bromophenyl)ethylidene)-2-methylpropane-2-sulfinamide (1.03 g, 3.4 mmol) in THF (2 mL) dropwise via a syringe. After 3 h add a saturated aqueous solution of NH4Cl (10 eq) and allow the mixture to warm to room temperature. Dilute the mixture with H2O (50 mL) and stir for 10 min, then partition the mixture between H2O (50 mL) and EtOAc (50 mL). Collect the organic layer and extract the aqueous layer with EtOAc (3×50 mL). Wash the combined organic extracts with brine, then dry (MgSO4), filter and concentrate to give a crude product. Chromatograph the crude product on a silica gel column and elute with EtOAc/hexanes to afford (S)-methyl 3-(3-bromophenyl)-3-((R)-1,1-dimethylethylsulfinamido)butanoate.

1. stirringAfter stirring for another 30 min
2. temperatureto warm to room temperature
3. stirringstir for 10 min
4. custompartition the mixture between H2O (50 mL) and EtOAc (50 mL)
5. customCollect the organic layer
6. extractionextract the aqueous layer with EtOAc (3×50 mL)
7. washWash the combined organic extracts with brine
8. dry with materialdry (MgSO4)
9. filtrationfilter
10. concentrationconcentrate
11. customto give a crude product
12. washChromatograph the crude product on a silica gel column and elute with EtOAc/hexanes

ORD record

ord-1336924440244fd9840525e4931bb5e3

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557826B2