Tetrahydrofuran → 3-(2,6-Dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid

HRID 19344노트

반응식

HRID 19344 반응식
C[O:2][C:3](=[O:29])[CH:4]([N:14]1[CH2:18][C:17]([O:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[CH:16][C:15]1=[O:28])[CH2:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:13].O1CCCC1.O.[OH-].[Li+]>O>[Cl:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([Cl:12])[C:6]=1[CH2:5][CH:4]([N:14]1[CH2:18][C:17]([O:19][C:20]2[C:21]([F:27])=[CH:22][CH:23]=[CH:24][C:25]=2[F:26])=[CH:16][C:15]1=[O:28])[C:3]([OH:29])=[O:2]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 668937393-(2,6-Dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

생성물 1

HCID 668948733-(2,6-Dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid수율 74%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

A mixture of 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (56 mg, 0.13 mmol) in a 1:1 solution of tetrahydrofuran:water (4 mL) was treated with lithium hydroxide monohydrate (11 mg, 0.26 mmol). The mixture was then stirred for 1 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with 1N aqueous hydrochloric acid until the pH was acidic and then extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (40 mg, 74%) as a tan solid: HR-ES-MS m/z calculated for C19H13NO4Cl2F2 [M+H]+ 428.0263, observed 428.0263.

후처리

  1. concentrationAfter such time, the mixture was concentrated in vacuo
  2. customto remove the tetrahydrofuran
  3. additiondiluted with 1N aqueous hydrochloric acid until the pH
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-90308d5bd24241f3af084306973d5996
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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