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Ammonia → tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

HRID 1350204
ノート
印刷プレビュー

反応式

HRID 1350204 の反応式
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:36]>C1COCC1.CCOC(C)=O>[NH2:36][CH2:24][C:21]1[N:20]=[C:19]([C@H:10]([CH2:9][CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:23][N:22]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 222AmmoniaHCID 16747945tert-Butyl (3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)1,2,4-oxadiazol-5-yl]hexanoate

生成物 1

HCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate収率 94%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

A soluton of tert-butyl(3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,2,4-oxadiazol-5-yl]hexanoate (preparation 177) (1.2 g, 2.37 mmol) in THF (40 ml) was treated with concentrated ammonia solution and heated in a bomb at 40° C. for 18 hours. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3 solution followed by brine. The organic extract was dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The colourless oil was purified on a silica column eluting with a solvent gradient of pentane:EtOAc (4:1) gradually changing to (1:1) and then changing to DCM:MeOH:NH3 (95:5:0.5) to afford the title compound as a colourless oil (782 mg, 94%).

後処理

  1. washwashed with sat. NaHCO3 solution
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe colourless oil was purified on a silica column
  7. washeluting with a solvent gradient of pentane:EtOAc (4:1)

出典と根拠

ORDレコード
ord-447e5dc0b6164fdc9bfc28568f0f7e09
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07214694B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート