Benzoyl chloride → tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate

HRID 1974

反応式

HRID 1974 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[C:1]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([P:24]([O:29][CH2:30][CH3:31])(=[O:28])[O:25][CH2:26][CH3:27])[P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 12102991Tetraethyl 5-aminopentane-1,1-bisphosphonate

生成物 1

HCID 19689031tetraethyl N-benzoyl-5-aminopentane-1,1-bisphosphonate収率 30.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of benzoyl chloride (0.73 g, 5.0 mmol) in dichloromethane was added slowly to a solution of tetraethyl 5-aminopentane-1,1-bisphosphonate (1.50 g, 4.5 mmol) from Example 11, part A, and triethylamine (0.76 mL, 5.5 mmol) in dichloromethane at 0° C. After warming to room temperature for 30 minutes, the reaction was quenched by addition of 1N HCl (30 mL). The product was extracted into dichloromethane (2×20 mL) and the combined organic layers were washed with saturated NaHCO3 (2×15 mL), dried (Na2SO4), and concentrated in vacuo. Flash chromatography on silica gel eluting with 15% i-propanol in ethylacetate in EtOAc gave the title compound (0.64 g) as an oil.

後処理

  1. customthe reaction was quenched by addition of 1N HCl (30 mL)
  2. extractionThe product was extracted into dichloromethane (2×20 mL)
  3. washthe combined organic layers were washed with saturated NaHCO3 (2×15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-18119a89941c4368a7ad288ebe54d59f
出典データセット
uspto-grants-1998_03
特許番号
US05728650

関連ノート

読み込み中…