반응 #2188937

반응 방정식

Boron trichloride methyl sulfide complex

6.4

(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

→

6.5

수율 63.0%

(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

수율 63.0%

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   기타the ice bath was removed
3. 3
   온도The mixture was cooled in an ice bath
4. 4
   기타quenched
5. 5
   workup.ADDITIONby adding saturated sodium bicarbonate until the mixture
6. 6
   workup.ADDITIONMore DCM (400 mL) was added
7. 7
   기타the organic layer was separated
8. 8
   세척washed with brine
9. 9
   기타dried
10. 10
    농축concentrated under vacuum
11. 11
    workup.DISSOLUTIONThe crude product (6.5 g) was dissolved in 50 mL of hot MeOH
12. 12
    온도After cooling
13. 13
    여과the crystallized product was collected by filtration
14. 14
    세척washed once with MeOH

실험 절차

Boron trichloride methyl sulfide complex (51 mL, 2.0 M solution in DCM) was added to 6.4 (8.2 g, 17 mmol) in DCM (100 mL) at 0° C. After addition, the ice bath was removed, and the mixture was stirred at room temperature for 7 hours. The mixture was cooled in an ice bath and quenched by adding saturated sodium bicarbonate until the mixture was neutralized. More DCM (400 mL) was added, and the organic layer was separated, washed with brine, dried, and concentrated under vacuum. The crude product (6.5 g) was dissolved in 50 mL of hot MeOH. After cooling, the crystallized product was collected by filtration and washed once with MeOH to give 6.5 (4.2 g). The filtrate was concentrated, and the solid that formed was collected and washed to give an additional 1.2 g of compound 6.5. MS ESI (pos.) m/e: 393 (M+H). 1H NMR (CDCl3) δ 8.29(d, 1H), 7.30 (m, 3H), 7.20 (d, 2H), 7.15 (d, 2H), 6.95 (d, 2H), 6.14 (d, 1H), 4.71 (dd, 1H), 4.63 (m, 1H), 4.16 (d, 2H), 4.00 (dd, 1H), 3.54 (dd, 1H), 3.21 (dd, 1H), 2.76 (dd, 1H).

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