Potassium Iodide → Ammonia

HRID 1433254Notes

Reaction equation

HRID 1433254 reaction equation
Cl.Cl.[CH2:3]([O:10][C:11]1[CH:25]=[CH:24][C:14]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[CH:13][C:12]=1[C@@H:26]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:27][CH2:28][N:29]([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:42]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:57]Br)=[CH:52][C:51]=1[NH:67][S:68]([CH3:71])(=[O:70])=[O:69])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(=O)([O-])O.[Na+].[I-].[K+]>[Cl-].[Na+].O.O.C(#N)C>[NH3:23].[CH2:42]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C@@H:56]([O:59][Si:60]([C:63]([CH3:64])([CH3:66])[CH3:65])([CH3:62])[CH3:61])[CH2:57][NH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:14]2[CH:24]=[CH:25][C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[C:12]([C@@H:26]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:27][CH2:28][N:29]([CH:33]([CH3:34])[CH3:35])[CH:30]([CH3:32])[CH3:31])[CH:13]=2)=[CH:52][C:51]=1[NH:67][S:68]([CH3:71])(=[O:69])=[O:70])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 866164817-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptan-1-amine bis hydrochloride salt

Product 2

HCID 222AmmoniaHCID 57933197N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptan-1-amine bis hydrochloride salt (Preparation 18, 190 mg, 0.31 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 161 mg, 0.32 mmol), sodium hydrogen carbonate (106 mg, 1.26 mmol) and potassium iodide (52 mg, 0.32 mmol) were added to acetonitrile (5 ml) and heated to 90° C. for 24 hours, then left at room temperature over night, water and brine were added and extracted with ethyl acetate, 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 (98/2/0.2 to 92/8/0.8 by volume) to furnish the title compound as a colourless gum, 100 mg.

Workup

  1. waitleft at room temperature over night
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (magnesium sulphate)
  4. customthe solvent removed in vacuo
  5. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-acf33986388b46c0a96c432668f54562
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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