Potassium Acetate → Ethyl (R)-2-[5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl]-4-thiazolidinecarboxylate

HRID 49011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49011
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3].C([O-])(=O)C.[K+].CC(C)=O.O.[CH3:21][N:22]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][C:25](=[O:32])[N:24]([C:33]2[CH:34]=[CH:35][C:36]3[S:40][N:39]=[C:38]([CH:41]=O)[C:37]=3[CH:43]=2)[C:23]1=[O:44]>CC(C)=O>[CH3:21][N:22]1[C:27]([C:28]([F:29])([F:30])[F:31])=[CH:26][C:25](=[O:32])[N:24]([C:33]2[CH:34]=[CH:35][C:36]3[S:40][N:39]=[C:38]([C@@H:41]4[NH:7][CH:6]([C:5]([O:4][CH2:2][CH3:3])=[O:10])[CH2:8][S:9]4)[C:37]=3[CH:43]=2)[C:23]1=[O:44]

Komponenten

6

Edukt 4

HCID 517044Potassium Acetate2×HCID 2723617Ethyl cysteinate hydrochloride2×HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehydeHCID 18366337Propan-2-one--water (1/1)

Produkt 1

HCID 86584515Ethyl (R)-2-[5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl]-4-thiazolidinecarboxylateAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of L-cysteine ethyl ester hydrochloride (0.580 g, 3.12 mmol), potassium acetate (0.300 g, 3.06 mmol) and 50% acetone-water is added dropwise a solution 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (1.00 g, 2.81 mmol) in acetone. The resultant mixture is stirred four days at room temperature and treated with additional L-cysteine ethyl ester hydrochloride (0.580 g, 3.12 mmol) and, potassium acetate (0.300 g, 3.06 mmol). The resultant mixture is warmed to 35° C. and stirred overnight. The mixture is concentrated in vacuo and the residue is extracted with methylene chloride. The organic layer is washed with water, treated with charcoal, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with methylene chloride-ethyl acetate to afford the title compound as an off-white solid (0.600 g, 43.9%, mp 97-98° C.) which is identified by NMR spectral analysis.

Aufarbeitung

  1. concentrationThe mixture is concentrated in vacuo
  2. extractionthe residue is extracted with methylene chloride
  3. washThe organic layer is washed with water
  4. additiontreated with charcoal
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel with methylene chloride-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4bcdb5ce65c444dcb364c33b7679caa5
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

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