Potassium Iodide → Ammonia

HRID 1433268ノート

反応式

HRID 1433268 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:24]Br)[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH2:36][CH2:37][CH2:38][C:39]1[CH:72]=[CH:71][C:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([C@@H:55]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)[CH2:56][CH2:57][N:58]([CH:62]([CH3:64])[CH3:63])[CH:59]([CH3:61])[CH3:60])[CH:49]=2)=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+].[I-].[K+].C(#N)CC>C(OCC)(=O)C>[NH3:36].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:23]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:24][NH:36][CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([C@@H:55]([C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)[CH2:56][CH2:57][N:58]([CH:59]([CH3:60])[CH3:61])[CH:62]([CH3:64])[CH3:63])[CH:49]=3)=[CH:71][CH:72]=2)[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium Bicarbonate2 回HCID 57683377{(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilaneHCID 866164804-{4-[4-(2-Aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

生成物 2

HCID 222AmmoniaHCID 579332204-(4-[4-(2-{[(2R)-2-[3,5-bis(benzyloxy)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

{(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilane (Prepared according to US2005/222128, 570 mg, 1.1 mmol), 4-{4-[4-(2-aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt (Preparation 13, 746 mg, 1.3 mmol), sodium hydrogen carbonate (544 mg, 6.48 mmol) and potassium iodide (50 mg, 0.30 mmol) were added to propionitrile (8 ml) and heated to 90° C. and left to stir overnight. After cooling, ethyl acetate and saturated aqueous sodium hydrogen carbonate were added, organics separated and washed with more saturated aqueous sodium hydrogen carbonate, then brine and then dried (magnesium sulphate) and solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100:0:0 to 94:6:0.6 by volume) to furnish the title compound as a yellow oil, 720 mg.

後処理

  1. waitleft
  2. temperatureAfter cooling
  3. customorganics separated
  4. washwashed with more saturated aqueous sodium hydrogen carbonate
  5. dry with materialbrine and then dried (magnesium sulphate) and solvent
  6. customremoved in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-f9012b7bcd2f4f87a7b7ed99acfa2ddb
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…