Diethyl (cyanomethyl)phosphonate → HCID 71143653、化合物

HRID 571458ノート

反応式

HRID 571458 の反応式
CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH:18]([NH:21][C:22](=[O:34])[C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:32][C:31](=O)[CH2:30]2)=[CH:25][CH:24]=1)([CH3:20])[CH3:19]>O1CCCC1>[C:7]([CH:9]=[C:31]1[CH2:32][N:29]([C:26]2[CH:27]=[CH:28][C:23]([C:22]([NH:21][CH:18]([CH3:20])[CH3:19])=[O:34])=[CH:24][CH:25]=2)[CH2:30]1)#[N:8]

参加物

5

反応物 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 71143526HCID 71143526、化合物

生成物 1

HCID 71143653HCID 71143653、化合物収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a cooled (at −6 to 0° C.) solution of 1.0 M potassium tert-butoxide in tetrahydrofuran (7.10 mL, 7.10 mmol) was added dropwise a solution of diethyl cyanomethylphosphonate (1.20 mL, 7.43 mmol, Aldrich: Cat. #D91705) in tetrahydrofuran (10.0 mL) over a period of 10 minutes and at −6 to 0° C. The reaction was warmed and stirred at room temperature for 1 hour. The reaction mixture was re-cooled at −6° C. To the reaction mixture was then added a solution of N-isopropyl-4-(3-oxoazetidin-1-yl)benzamide (1.30 g, 5.60 mmol) in tetrahydrofuran (10.0 mL) over a period of 10 minutes. During this time the temperature of the reaction mixture was between −5 to 0° C. The reaction was allowed to warm to room temperature and was stirred for 3 hours. The reaction mixture was filtered through a pad of silica gel and washed with ethyl acetate. The filtrate was concentrated, and the residue was treated with ether. The precipitates formed were collected by filtration to give 0.60 g desired product. The mother liquid was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (gradient: 30-80%) to afford the desired product (0.21 g). the total product is 0.81 g (57%). LCMS (M+H)+: m/z=256.1.

後処理

  1. customat −6 to 0° C
  2. temperatureThe reaction was warmed
  3. temperatureThe reaction mixture was re-cooled at −6° C
  4. customwas between −5 to 0° C
  5. temperatureto warm to room temperature
  6. stirringwas stirred for 3 hours
  7. filtrationThe reaction mixture was filtered through a pad of silica gel
  8. washwashed with ethyl acetate
  9. concentrationThe filtrate was concentrated
  10. additionthe residue was treated with ether
  11. customThe precipitates formed
  12. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-94ef180b40b445899f72d9cd76d5e507
出典データセット
uspto-grants-2015_05
特許番号
US09023840B2

反応ノート

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