Triphenylphosphine → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

HRID 2224622ノート

反応式

HRID 2224622 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[C:4]([C@H:26](O)[CH3:27])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C@H:26]2[CH3:27]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69253499N-{4'-Fluoro-2'-[(R)-1-hydroxyethyl]-1,1'-biphenyl-2-yl}-4-methoxybenzenesulfonamide

生成物 1

HCID 58597403(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-{4′-fluoro-2′-[(1R)-1-hydroxyethyl]-1,1′-biphenyl-2-yl}-4-methoxybenzene-sulfonamide (0.12 g, 0.29 mmol) and triphenylphosphine (0.31 g, 1.2 mmol) were dissolved in tetrahydrofuran (10 mL) and diethylazodicarboxylate (0.21 g, 0.19 mL, 1.2 mmol) was added. The solution was stirred overnight at room temperature. The solution was concentrated in vacuo and the mixture was dissolved in ethyl acetate and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (3:1 hexane: ethyl acetate) to yield the title compound as a crystalline solid (0.085 g, 79% ), m.p. 181-182° C.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe mixture was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (3:1 hexane: ethyl acetate)

出典と根拠

ORDレコード
ord-90fdedd721a241f986fa99897b5f00d8
出典データセット
uspto-grants-2008_05
特許番号
US07378427B2

反応ノート

読み込み中…