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 237700ノート

反応式

HRID 237700 の反応式
[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

参加物

7

反応物 3

HCID 5462222Potassium2 回HCID 23707502Potassium hydroxy sulfite2 回HCID 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

生成物 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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-db67fb1385d7498ca93375862bb18a48
出典データセット
uspto-grants-2014_02
特許番号
US08642585B2

反応ノート

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