تفاعل #616625

معادلة التفاعل

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

THF

water

H2O2

→

(2S,5S,E)-2-benzyl-5-(3-tert-butoxy-3-oxopropyl)hex-3-enedioic acid

المردود 63.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched by the addition of saturated Na2SO3 (0.38 mL) and saturated NaHCO3 (0.38 mL)
2. 2
   تركيزThe mixture was concentrated
3. 3
   أخرىto remove most of the THF
4. 4
   workup.ADDITIONThe mixture was diluted with a small amount of water
5. 5
   استخلاصextracted with EtOAc (2×)
6. 6
   أخرىto remove chiral auxiliary
7. 7
   استخلاصextracted with EtOAc (2×)
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated

الإجراء التجريبي

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.

المصدر