(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester

HRID 11907

Reaktionsgleichung

Reaktionsgleichung von HRID 11907
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2=[N:10][C:11]([Cl:14])=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([CH3:34])OS1(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:15]([C@H:32]([CH3:34])[CH2:33][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:9]2=[N:10][C:11]([Cl:14])=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 21868758Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 86760224(R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3.0 g (13.3 mmol) 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester in 70 ml N,N-dimethylformamide was cooled to 0 deg C. and 1.58 g (14.0 mmol) potassium tert-butoxide was added. After 30 min, 3.49 g (14.7 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester was added in one portion. The cooling bath was removed and after 1.5 h the reaction mixture was poured into 100 ml 10% aqueous citric acid. The layers were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed four times with water, once with brine and then were dried over magnesium sulfate. After filtration the solvent was removed on a rotary evaporator and the residue was purified by flash-chromatography over silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (9:1, then 5:1) as eluant to afford the product as a yellow oil (98.0%).

Aufarbeitung

  1. customThe cooling bath was removed and after 1.5 h the reaction mixture
  2. additionwas poured into 100 ml 10% aqueous citric acid
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic phases were washed four times with water
  6. dry with materialonce with brine and then were dried over magnesium sulfate
  7. filtrationAfter filtration the solvent
  8. customwas removed on a rotary evaporator
  9. customthe residue was purified by flash-chromatography over silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (9:1

Quellen und Nachweise

ORD-Eintrag
ord-c54cdbd8852148ac91f1b58babbae954
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098337B2

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