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

HRID 879347ノート

反応式

HRID 879347 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-468c3529563e4adf986630908bf4a1ed
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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