Perchloric Acid → (S)-ethyl 2-tert-butoxy-2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

HRID 879347노트

반응식

HRID 879347 반응식
[Cl:1][C:2]1[S:3][C:4]2[C:10]([O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[C:9]([C@H:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1.Cl(O)(=O)(=O)=O.[C:32](O[C@@H](C1C(C)=CC2N=C(Br)SC=2C=1OS(C(F)(F)F)(=O)=O)C(OCC)=O)([CH3:35])([CH3:34])[CH3:33]>C(OC(C)(C)C)(=O)C>[C:32]([O:25][C@@H:19]([C:9]1[C:8]([CH3:26])=[CH:7][C:5]2[N:6]=[C:2]([Cl:1])[S:3][C:4]=2[C:10]=1[O:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[O:14])=[O:13])[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:35])([CH3:34])[CH3:33]

참가 물질

5

반응물 3

HCID 24247Perchloric AcidHCID 86699785(S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700144(S)-ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetate

생성물 1

HCID 86700146(S)-ethyl 2-tert-butoxy-2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

실험 절차

To a solution of (S)-ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetate (0.5691 g, 1.31 mmol) in tert-butyl acetate (65 mL) was added 70% perchloric acid (65 μL, 1.57 mmol). Reaction mixture was stirred for 1.5 h and quenched with solid sodium bicarbonate. Saturated sodium bicarbonate solution was carefully added until basic and mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 15% EtOAc/Hex) to give product contaminated with (S)-ethyl 2-tert-butoxy-2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate. 1H NMR (400 MHz, CDCl3): δ 7.78 (s, 1H), 5.59 (s, 1H), 4.4-4.1 (m, 2H), 2.55 (s, 3H), 1.20 (s, 9H), 1.16 (t, J=7.2 Hz, 3H).

후처리

  1. customReaction mixture
  2. customquenched with solid sodium bicarbonate
  3. additionSaturated sodium bicarbonate solution was carefully added until basic and mixture
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate solution, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by CombiFlash (0 to 15% EtOAc/Hex)
  10. customto give product

출처 및 근거

ORD 기록
ord-468c3529563e4adf986630908bf4a1ed
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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