Tetrahydrofuran → 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acid

HRID 1881904노트

반응식

HRID 1881904 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][C@H:19]2[CH2:39][CH2:38][C:21]3([O:25][C@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:22]3)[CH2:20]2)[C:13]([O:15]CC)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].O1CCCC1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:18][C@H:19]2[CH2:39][CH2:38][C:21]3([O:22][C@H:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C@@H:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[O:25]3)[CH2:20]2)[C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59331567ethyl 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoate

생성물 1

HCID 593314112-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoic acid수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of ethyl 2-[3-chloro-4-(methylsulfonyl)phenyl]-3-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]propanoate in a mixed solvent of tetrahydrofuran (200 mL) and methanol (100 mL) was added 2M aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, the residue was acidified with 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio) to give the title compound (17.6 g, yield 97%) as a colorless amorphous solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio)

출처 및 근거

ORD 기록
ord-ef83317fe35f438d8b41f26bab55f2ce
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

반응 노트

불러오는 중…