Potassium Iodide → Ammonia

HRID 1433271ノート

反応式

HRID 1433271 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].CS(O[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:35]([C@@H:47]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[CH2:48][CH2:49][N:50]([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:53])[CH3:52])[CH:34]=1)(=O)=O>CN(C)C=O.C(OCC)C.O>[NH3:7].[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[C:35]([C@@H:47]([C:57]3[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=3)[CH2:48][CH2:49][N:50]([CH:54]([CH3:55])[CH3:56])[CH:51]([CH3:52])[CH3:53])[CH:34]=2)[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

9

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11031911tert-Butyl 3-hydroxyphenethylcarbamateHCID 579331664-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenylethyl methanesulfonate

生成物 2

HCID 222AmmoniaHCID 57933226tert-butyl {2-[3-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}carbamate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

tert-butyl[2-(3-hydroxyphenyl)ethyl]carbamate (Preparation 35, 1.7 g, 5.96 mmol), potassium carbonate (1.65 g, 11.9 mmol), potassium iodide (5.0 g, 0.03 mmol) and 2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl)ethyl methanesulfonate (Preparation 36, 1.56 g, 2.98 mmol) were stirred in dimethylformamide (20 ml) and stirred at 60° C. overnight. After cooling, water (250 ml) and diethyl ether (250 ml) were added, organics separated and washed with water (100 ml×3), brine (150 ml) then dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 90/10/1.0 by volume) to furnish the title compound as an oil, 1.3 g.

後処理

  1. temperatureAfter cooling
  2. customorganics separated
  3. washwashed with water (100 ml×3), brine (150 ml)
  4. dry with materialthen dried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-5345daf01ef04edfabd1c66772b16be1
出典データセット
uspto-grants-2009_11
特許番号
US07612084B2

反応ノート

読み込み中…