Ammonium Chloride → (9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 2249711

反応式

HRID 2249711 の反応式
[NH2:1][C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][C:16]1[N:17]=[C:18]2[C:23](=O)[CH2:22][CH2:21][CH2:20][N:19]2[C:25]=1[CH3:26].CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:15][C:16]1[N:17]=[C:18]2[C:23]3[NH:1][C@H:2]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:3][C:4](=[O:6])[C:22]=3[CH2:21][CH2:20][N:19]2[C:25]=1[CH3:26]

参加物

9

反応物 4

HCID 25517Ammonium ChlorideHCID 915085(S)-Ethyl 3-amino-3-phenylpropanoateHCID 113556692,3-dimethyl-5H,6H,7H,8H-imidazo[1,2-a]pyridin-8-oneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 69288840(9S)-2,3-Dimethyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one収率 88%

試薬・触媒・溶媒 4

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

9.7 g (51.6 mmol) of ethyl (S)-3-amino-3-phenylpropionate, 8.5 g (51.6 mmol) of 2,3-dimethyl-6,7-dihydro-5H-imidazo[1,2-a]pyridin-8-one and 0.26 g (1.3 mmol) of p-toluenesulphonic acid monohydrate are heated to reflux in 50 ml of toluene using a water separator. After no more water separates, the reaction mixture is cooled to 0° C. and diluted with 100 ml of tetrahydrofuran. 7.24 g (64.5 mmol) of potassium tert-butoxide are then introduced and the mixture is stirred at room temperature for 16 h. 150 ml of saturated ammonium chloride are added to the reaction mixture, the organic phase is removed and the aqueous phase is extracted with 300 ml of ethyl acetate. The combined organic phases are washed with 250 ml of water, dried over sodium sulphate and evaporated. 13.27 g (88%) of the title compound are isolated as a red-brown oil. An analytical sample is obtained by crystallizing with diethyl ether (red solid, m.p. 134° C.).

後処理

  1. customthe organic phase is removed
  2. extractionthe aqueous phase is extracted with 300 ml of ethyl acetate
  3. washThe combined organic phases are washed with 250 ml of water
  4. dry with materialdried over sodium sulphate
  5. customevaporated

出典と根拠

ORDレコード
ord-39de779ebc194ab4b2b306cc2142529c
出典データセット
uspto-grants-2008_01
特許番号
US07314935B2

関連ノート

読み込み中…