Sodium Hydroxide → HCID 67340549, 화합물

HRID 1670130노트

반응식

HRID 1670130 반응식
C([O:3][C:4](=[O:48])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=3)[CH:25]=[C:26]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH:27]=2)[C:10]=1[CH2:41][CH2:42][C:43]([O:45]CC)=[O:44])C.[OH-].[Na+]>C1COCC1.C(O)C>[C:43]([CH2:42][CH2:41][C:10]1[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([F:40])[CH:34]=3)[CH:25]=[C:26]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH:27]=2)=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:48])=[O:3])([OH:45])=[O:44]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67339165HCID 67339165, 화합물

생성물 1

HCID 67340549HCID 67340549, 화합물수율 95.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-{3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (143 mg, 0.214 mmol) in THF (5 mL) and ethanol (5 mL) was added aqueous 1.0 N sodium hydroxide (5 mL) at room temperature. The mixture was stirred for 7 h at room temperature. Then, the reaction mixture was concentrated, the residue was diluted with water (20 mL) and extracted with diethyl ether (50 mL) to remove any neutral impurities. The aqueous layer was acidified with 1 N hydrochloric acid and the organic compound was extracted into ethyl acetate (2×50 mL). The combined organic extracts were washed with brine solution (50 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under vacuum gave 4-{2-(2-carboxy-ethyl)-3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-phenoxy}-butyric acid (125 mg, 95%) as a white amorphous solid.

후처리

  1. concentrationThen, the reaction mixture was concentrated
  2. additionthe residue was diluted with water (20 mL)
  3. extractionextracted with diethyl ether (50 mL)
  4. customto remove any neutral impurities
  5. extractionthe organic compound was extracted into ethyl acetate (2×50 mL)
  6. washThe combined organic extracts were washed with brine solution (50 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationFiltration of the drying agent and removal of the solvent under vacuum

출처 및 근거

ORD 기록
ord-e9b7558008f4425a9d287c97492e101a
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989454B2

반응 노트

불러오는 중…