Benzcatechinborane → (S)-ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetate

HRID 879346노트

반응식

HRID 879346 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:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]([CH3:26])=[CH:7][C:5]=2[N:6]=1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[B]1OC2C(=CC=CC=2)O1.BrC1SC2C(OS(C(F)(F)F)(=O)=O)=C([C@H](O)C(OCC)=O)C(C)=CC=2N=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[S:3][C:4]2[C:10]([O:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[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

참가 물질

6

반응물 4

HCID 6327445BenzcatechinboraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 86699783(S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetateHCID 86700145Ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate

생성물 1

HCID 86700144(S)-ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetate

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a solution of ethyl 2-(2-chloro-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-oxoacetate (0.6621 g, 1.53 mmol), and (R)-2-methyl-CBS-oxazaborolidine (0.098 g, 0.35 mmol) in toluene (6 mL) was added a solution of distilled catecholborane (0.254 g, 2.39 mmol) in toluene (1 mL) over 15 minutes, then stirred for another 45 minutes. The reaction was quenched with saturated sodium carbonate solution and stirred at room temperature for 15 minutes. Product extracted with EtOAc and organic layer washed with saturated sodium carbonate (3×), brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 25% EtOAc/Hex) to give product contaminated with (S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-hydroxyacetate. LCMS-ESI+: calc'd for C13H12ClF3NO6S2: 434.0 (M+H+); Found: 433.9 (M+H+).

후처리

  1. customThe reaction was quenched with saturated sodium carbonate solution
  2. stirringstirred at room temperature for 15 minutes
  3. extractionProduct extracted with EtOAc and organic layer
  4. washwashed with saturated sodium carbonate (3×), brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CombiFlash (0 to 25% EtOAc/Hex)
  9. customto give product

출처 및 근거

ORD 기록
ord-c46be5521dc040f3a29cfa9e44e11078
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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