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Potassium Iodide → Ammonia

HRID 1433277
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HRID 1433277 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:44]=[CH:43][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:17]([C@@H:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=2)=[CH:8][CH:7]=1.[CH2:45]([O:52][C:53]1[CH:54]=[C:55]([C@@H:67]([O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72])[CH2:68]Br)[CH:56]=[C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:58]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[I-].[K+].C(=O)([O-])O.[Na+].C(#N)CC>C(OCC)(=O)C.O>[NH3:3].[CH2:36]([O:35][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][O:10][C:9]2[CH:43]=[CH:44][C:6]([CH2:5][CH2:4][NH:3][CH2:68][C@@H:67]([C:55]3[CH:54]=[C:53]([O:52][CH2:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:58]=[C:57]([O:59][CH2:60][C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH:56]=3)[O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72])=[CH:7][CH:8]=2)=[CH:18][C:17]=1[C@@H:19]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium BicarbonateHCID 57683377{(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilaneHCID 86616485(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt

생성물 2

HCID 222
Ammonia
HCID 57933155(3R)-3-[2-(benzyloxy)-5-{2-[4-(2-{[(2R)-2-[3,5-bis(benzyloxy)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]ethyl}phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt (Preparation 42, 600 mg, 0.94 mmol), {(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilane (Prepared according to US2005/222128, 500 mg, 0.94 mmol), potassium iodide (160 mg, 0.94 mmol), sodium hydrogen carbonate (480 mg, 5.65 mmol) were added to propionitrile (10 ml) and stirred at 100° C. under nitrogen overnight. The mixture was cooled and water (75 ml) and ethyl acetate (75 ml) were added. Organics were separated and washed with brine (25 ml), 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 by volume) to furnish the title compound as a gum, 346 mg.

후처리

  1. temperatureThe mixture was cooled
  2. customOrganics were separated
  3. washwashed with brine (25 ml)
  4. dry with materialdried (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-c2e413cb37d94546bc928e0e57fba51e
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612084B2

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