Citric Acid → 3-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamide

HRID 1250997

반응식

HRID 1250997 반응식
[CH:1]1([N:7]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])C(=O)CC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Mg]Cl)(CC)C.C(O[C@H:32]1[NH:35][C:34](=[O:36])[C@@H:33]1[C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])(=O)C.[C:47](O)(=O)[CH2:48][C:49](CC(O)=O)(C(O)=O)[OH:50]>O1CCCC1.C(OCC)(=O)C>[Si:40]([O:39][C@@H:37]([C@@H:33]1[C@@H:32]([C@@H:48]([CH3:47])[C:49]([C:20]2[CH:19]=[C:18]([CH3:21])[CH:17]=[CH:16][C:15]=2[S:12]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)(=[O:13])=[O:14])=[O:50])[NH:35][C:34]1=[O:36])[CH3:38])([C:43]([CH3:44])([CH3:45])[CH3:46])([CH3:41])[CH3:42]

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 10935078AzetidonHCID 18325691N-cyclohexyl-N-p-toluenesulfonylpropionamideHCID 178418314HCID 178418314, 화합물

생성물 1

HCID 699481593-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamide수율 63%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

Under a nitrogen atmosphere, 309 mg (1.0 mmol) of N-cyclohexyl-N-p-toluenesulfonylpropionamide was charged in a 30-ml three-necked flask to dissolve it in 2 ml of tetrahydrofuran. To the resulting solution, 2.2 ml (2.2 mmol) of a tetrahydrofuran solution (0.99M) of sec-butylmagnesium chloride was slowly added dropwise at room temperature. The resulting mixture was reacted for 25 minutes under the same conditions. After cooling to 5° C., 2 ml of a tetrahydrofuran solution of 287 mg (1.0 mmol) of (3R,4R)-4-acetoxy-3-[(R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one was added at the same temperature. The resulting mixture was stirred for 10 minutes, added with 10 ml of ethyl acetate and then added dropwise with 2 ml of a 10% aqueous solution of citric acid. After separation, the organic layer was washed with 2 ml of a saturated aqueous solution of sodium bicarbonate and 2 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by column chromatography, whereby 339 mg of a condensation product was obtained (yield: 63%, β:α=92:8).

후처리

  1. customThe resulting mixture was reacted for 25 minutes under the same conditions
  2. customAfter separation
  3. washthe organic layer was washed with 2 ml of a saturated aqueous solution of sodium bicarbonate and 2 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4036d989b0d04f639287d2bcd0209ed2
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06340751B1

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