Sodium borohydride → 3-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid

HRID 1582992ノート

反応式

HRID 1582992 の反応式
C1COCC1.C(O)C.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][C:22]([CH:26]=[O:27])=[CH:23][CH:24]=3)[N:19]([CH2:28][CH3:29])[C:18](=[O:30])[C:17]=2[CH2:31][CH2:32][C:33]([O:35]C)=[O:34])[CH:13]=[CH:14][CH:15]=1.[BH4-].[Na+]>O>[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[N:21][C:22]([CH2:26][OH:27])=[CH:23][CH:24]=3)[N:19]([CH2:28][CH3:29])[C:18](=[O:30])[C:17]=2[CH2:31][CH2:32][C:33]([OH:35])=[O:34])[CH:13]=[CH:14][CH:15]=1

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 22716671Methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate

生成物 1

HCID 227167153-[4-(3-Chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid収率 44.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a 7 ml THF-ethanol (5:2) solution containing 300 mg of methyl 3-[4-(3-chlorophenyl)-1-ethyl-7-formyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoate was added 9 mg of sodium borohydride under ice cooling. After stirring for 1 hour, water was added to the reaction mixture and the whole was extracted with ethyl acetate. The organic layer was washed with saturated brine and then the solvent was evaporated. The residue was purified by a silica gel column chromatography (hexane-ethyl acetate). Using a 200 mg portion of 210 mg of the resulting compound, the compound was treated in a similar manner to Example 2 to obtain 130 mg of 3-[4-(3-chlorophenyl)-1-ethyl-7-hydroxymethyl-2-oxo-1,2-dihydro-1,8-naphthyridin-3-yl]propanoic acid as pale yellow crystals.

後処理

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by a silica gel column chromatography (hexane-ethyl acetate)
  5. additionthe compound was treated in a similar manner to Example 2

出典と根拠

ORDレコード
ord-bcd2d925c3fd4e679edc41f5bd15465e
出典データセット
uspto-grants-2004_05
特許番号
US06740662B1

反応ノート

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