(S)-(+)-Glycidyl-4-nitrobenzoate → ethyl (S)-4-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)-1-(2-methylpropyl)indole-2-carboxylate

HRID 460564

反応式

HRID 460564 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:6]2[CH2:11][CH:12]([CH3:14])[CH3:13].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:24][C@H:25]1[O:27][CH2:26]1)(=O)=O.[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1[CH:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>>[OH:27][C@@H:25]([CH2:26][N:50]1[CH2:51][CH2:52][CH:47]([C:38]2[CH:39]=[CH:40][C:41]3[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:37]=2)[CH2:48][CH2:49]1)[CH2:24][O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:6]2[CH2:11][CH:12]([CH3:14])[CH3:13]

参加物

4

実験手順

By the reactions in the same manner as in Starting Material Synthesis Example 25 using ethyl 4-hydroxy-1-(2-methylpropyl)indole-2-carboxylate (5.0 g) obtained in Starting Material Synthesis Example 12, (S)-glycidyl nosylate (4.5 g) and 4-(naphthalen-2-yl)piperidine (5.3 g), ethyl (S)-4-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)-1-(2-methylpropyl)indole-2-carboxylate (7.5 g) was obtained. This was dissolved in ethanol (40 ml) and water (30 ml) and potassium hydroxide (4.0 g) were added. The mixture was refluxed for 2.5 hr. From the obtained reaction mixture, ethanol was evaporated under reduced pressure and 1N aqueous hydrochloric acid solution (30 ml) was added under ice-cooling. The mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and isopropyl ether was added to the obtained oil. The obtained crystals were collected by filtration to give the title compound (6.7 g) as pale-yellow crystals.

後処理

  1. customobtained

出典と根拠

ORDレコード
ord-fce260f4538047b79c9d27d1079688cb
出典データセット
uspto-grants-2007_03
特許番号
US07196199B2

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