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

HRID 1582992노트

반응식

HRID 1582992 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcd2d925c3fd4e679edc41f5bd15465e
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740662B1

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