Hydrogen Peroxide → HCID 68292050, compound

Temperature

0 °C

To a round bottom flask was added tert-butyl (4S,5E,7S)-7-benzyl-8-((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)-4-(((7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzothiazol-1(3H,4H)-yl)carbonyl)-8-oxooct-5-enoate (78 mg, 0.10 mmol), THF (0.8 mL) and water (0.25 mL). The reaction was cooled to 0° C. and a solution of H2O2 (50% in water, 0.038 mL, 0.62 mmol) was added to the reaction mixture followed by LiOH monohydrate (13.0 mg, 0.309 mmol). The reaction was stirred at 0° C. for 35 min. The reaction was quenched by the addition of saturated Na2SO3 (0.38 mL) and saturated NaHCO3 (0.38 mL). The mixture was concentrated to remove most of the THF. The mixture was diluted with a small amount of water and extracted with EtOAc (2×) to remove chiral auxiliary. The aqueous phase was then acidified and extracted with EtOAc (2×). The organic extracts were combined, dried over MgSO4, filtered and concentrated to give (2S,5S,E)-2-benzyl-5-(3-tert-butoxy-3-oxopropyl)hex-3-enedioic acid (24 mg, 0.065 mmol, 63% yield) as a colorless solid.

1. customThe reaction was quenched by the addition of saturated Na2SO3 (0.38 mL) and saturated NaHCO3 (0.38 mL)
2. concentrationThe mixture was concentrated
3. customto remove most of the THF
4. additionThe mixture was diluted with a small amount of water
5. extractionextracted with EtOAc (2×)
6. customto remove chiral auxiliary
7. extractionextracted with EtOAc (2×)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-48067bbf95d34ce1a5982da97025f8ce

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346852B2