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

HRID 879346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879346
[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

Komponenten

6

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c46be5521dc040f3a29cfa9e44e11078
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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