Potassium → 2-((S)-6-((R)-4-(2,6-Dimethyl-4-(2-(methylsulfonyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 237700노트

반응식

HRID 237700 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][S:11]([CH3:13])=[O:12])[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:38]=[CH:37][C:29]2[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1.[K].[OH:40]OS([O-])=O.[K+]>CO.O.C(#N)C.O>[CH3:14][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][S:11]([CH3:13])(=[O:40])=[O:12])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]2[C:16]=1[CH2:17][CH2:18][C@H:19]2[O:25][C:26]1[CH:38]=[CH:37][C:29]2[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=2[CH:27]=1

참가 물질

7

반응물 3

HCID 5462222Potassium2회HCID 23707502Potassium hydroxy sulfite2회HCID 717389962-((3S)-6-((1R)-4-(2,6-Dimethyl-4-(2-(methylsulfinyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

생성물 1

HCID 717389972-((S)-6-((R)-4-(2,6-Dimethyl-4-(2-(methylsulfonyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

To a solution of 2-((3S)-6-((1R)-4-(2,6-dimethyl-4-(2-(methylsulfinyl)ethoxy)phenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetic acid (70 mg) in methanol (1.5 mL) and water (0.75 mL) is added potassium peroxomonoslufate (Oxone®) (150 mg). The mixture is stirred for 3 hour at room temperature and then potassium peroxomonoslufate (Oxone®) (80 mg) is added. After stirring for 12 hours at room temperature the mixture is partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100). The product thus obtained is dissolved in acetonitrile/water (1:1) and lyophilized to give the title compound. Yield: 7 mg; LC (method 4): tR=1.71 min; Mass spectrum (ESI+): m/z=555 [M+H]+.

후처리

  1. stirringAfter stirring for 12 hours at room temperature the mixture
  2. customis partitioned between ethyl acetate and water
  3. dry with materialThe organic phase is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 50:50→0:100)
  6. customThe product thus obtained

출처 및 근거

ORD 기록
ord-db67fb1385d7498ca93375862bb18a48
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642585B2

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