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

HRID 1827684
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반응식

HRID 1827684 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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, 4-9 (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 4-10 as a yellow oil.

후처리

  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)

출처 및 근거

ORD 기록
ord-7bd1db15ce7d4404ac79c47b98112351
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07056909B2

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