Potassium Iodide → Ammonia

HRID 1433271노트

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HRID 1433271 반응식
[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]

참가 물질

9

반응물 4

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

생성물 2

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5345daf01ef04edfabd1c66772b16be1
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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