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

HRID 1250997

反応式

HRID 1250997 の反応式
[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]

参加物

7

反応物 4

HCID 311Citric AcidHCID 10935078AzetidonHCID 18325691N-cyclohexyl-N-p-toluenesulfonylpropionamideHCID 178418314HCID 178418314、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4036d989b0d04f639287d2bcd0209ed2
出典データセット
uspto-grants-2002_01
特許番号
US06340751B1

関連ノート

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