Potassium Iodide → Ammonia

HRID 1433275노트

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HRID 1433275 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][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>C1(C)C=CC=CC=1.C(OCC)(=O)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][C:13]([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:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

9

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateHCID 579331664-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenylethyl methanesulfonate

생성물 2

HCID 222AmmoniaHCID 57933204tert-butyl {2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}carbamate

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

tert-butyl[2-(4-hydroxyphenyl)ethyl]carbamate (Prepared according to WO1998/43942, 3.8 g, 7.3 mmol), potassium carbonate (2.6 g, 8.0 mmol), potassium iodide (1.1 g, 7.3 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 toluene (20 ml) and stirred at 120° C. overnight. After cooling, water (80 ml) and ethyl acetate (80 ml) were added, organics separated and washed with saturated aqueous sodium hydrogen carbonate (40 ml), brine (40 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 (99/1/0.1 to 90/10/1.0 by volume) to furnish the title compound as an oil, 3.4 g.

후처리

  1. temperatureAfter cooling
  2. customorganics separated
  3. washwashed with saturated aqueous sodium hydrogen carbonate (40 ml), brine (40 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-c5aa7cf2590f4829b357376bd55dca1c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612084B2

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