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Citric Acid → HCID 66643735, 화합물

HRID 1695429
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HRID 1695429 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])[CH:9]=1)=[O:4].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4]
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참가 물질

5

반응물 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 86647276HCID 86647276, 화합물

생성물 1

HCID 66643735HCID 66643735, 화합물수율 70.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 5-[3-(4-fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (720 mg, 2.0 mmol) and sodium borohydride (158 mg, 4.0 mmol) in methanol (36 mL) were stirred for 1 h at room temperature. Addition of 10% aqueous citric acid (100 mL) was followed by extraction with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (510 mg, 70%) as a white solid. MS: m/e=420.3 [M+OAc]−.

후처리

  1. extractionwas followed by extraction with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

출처 및 근거

ORD 기록
ord-fe0558ed2431440c8c5c1099e2888d79
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163728B2

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