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Lithium hydroxide, monohydrate → 4-Oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid

HRID 1497697
ノート
印刷プレビュー

反応式

HRID 1497697 の反応式
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:4]=[C:3]1[C:29]([O:31]CC)=[O:30].O.[OH-].[Li+]>CS(C)=O.CO.O.C(#N)C>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:4]=[C:3]1[C:29]([OH:31])=[O:30]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725449Ethyl 4-oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylate

生成物 1

HCID 769026754-Oxo-1-((4'-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid収率 43.2%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒
HCID 887
Methanol
溶媒
HCID 962Water溶媒2 回
HCID 6342Acetonitrile溶媒

実験手順

To a solution of ethyl 4-oxo-1-((4′-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylate (37) (11 mg, 0.024 mmol) in dimethyl sulfoxide (1 mL) and methanol (5 mL) was added the solid lithium hydroxide monohydrate (51.0 mg, 1.22 mmol) at room temperature under a nitrogen atmosphere. It gave a clear solution within 30 minutes and this light yellow solution was stirred for 15 h at which time LCMS analysis indicated the absence of starting material. Then, the mixture was diluted with water and the methanol was removed under vacuum. The basic aqueous layer was diluted with water and then neutralized with 1.0N HCl. The resulting acid was extracted with ethyl acetate (2×30 mL) and the combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave a brown residue which was dissolved in acetonitrile and water. It was frozen and then lyophilized under high vacuum to obtain 4-oxo-1-((4′-(trifluoromethyl)biphenyl-2-yl)methyl)-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid (38) (4.4 mg, 42.6% yield) as a light yellow solid.

後処理

  1. customIt gave a clear solution within 30 minutes
  2. customthe methanol was removed under vacuum
  3. additionThe basic aqueous layer was diluted with water
  4. extractionThe resulting acid was extracted with ethyl acetate (2×30 mL)
  5. washthe combined extracts were washed with brine solution
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltration and concentration
  8. customgave a brown residue which
  9. temperatureIt was frozen

出典と根拠

ORDレコード
ord-26ff61e305004141b2d466ea1a72fd96
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09199987B2

反応ノート

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