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Dimethyl methylphosphonate → [2-Oxo4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-butyl]-phosphonic acid dimethyl ester

HRID 2187375
ノート
印刷プレビュー

反応式

HRID 2187375 の反応式
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].[Li]CCCC.C([O:15][C:16](=O)[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][NH:22][C:21]=2[N:20]=1)C>C1COCC1>[CH3:4][O:3][P:2]([CH2:1][C:16](=[O:15])[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[CH2:25][CH2:24][CH2:23][NH:22][C:21]=2[N:20]=1)(=[O:7])[O:5][CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 12958Dimethyl methylphosphonateHCID 23581268Ethyl 3-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-YL)propanoateHCID 178418339Butyllithium

生成物 1

HCID 22082659[2-Oxo4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-butyl]-phosphonic acid dimethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of dimethyl methylphosphonate (1.9 mL, 17.08 mmol) in THF (20 mL) at −78° C. was added nBuLi (10.94 mL, 17.5 mmol). After 30 minutes, 2-9 (1 g , 4.27 mmol) in THF (5 mL) was added. After 1 hour, the reaction was quenched with saturated NH4Cl (10 mL) and warmed to ambient temperature. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH) to give 2-10 as a yellow oil.

後処理

  1. waitAfter 1 hour
  2. customthe reaction was quenched with saturated NH4Cl (10 mL)
  3. additionThe mixture was diluted with ethyl acetate
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH)

出典と根拠

ORDレコード
ord-e116231e76f1462e9b80faa332487526
出典データセット
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06410526B1

反応ノート

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