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 49011노트

반응식

HRID 49011 반응식
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]

참가 물질

6

반응물 4

HCID 517044Potassium Acetate2회HCID 2723617Ethyl cysteinate hydrochloride2회HCID 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)

생성물 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-thiazolidinecarboxylate수율 43.9%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4bcdb5ce65c444dcb364c33b7679caa5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706663B2

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