Hydrochloric Acid → 4-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid

HRID 2190124노트

반응식

HRID 2190124 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([O:24]CC)=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[Li+].O.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([OH:24])=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58064795Ethyl 4-(3-chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylate

생성물 1

HCID 580647984-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1.05 g (2.84 mmol) of the compound from Example 11A are provided in 30 ml of tetrahydrofuran, and 0.68 g (28.4 mmol) of lithium hydroxide and 10 ml of water are added at room temperature. The mixture is stirred at room temperature overnight, a 1N aqueous HCl solution is then added until an acidic pH is established, the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 0.60 g (62% of theory) of the title compound are obtained.

후처리

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

출처 및 근거

ORD 기록
ord-46d158c42a2b48838d1998c0095c319d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324268B2

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