Potassium Iodide → Ammonia

HRID 1433262Notes

Reaction equation

HRID 1433262 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([C@@H:20]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:21][CH2:22][N:23]([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:14]=1.[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([C@@H:50]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH2:51]Br)=[CH:46][C:45]=1[NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[I-].[K+].C(=O)([O-])O.[Na+]>C(#N)CC>[NH3:1].[CH2:36]([O:43][C:44]1[CH:49]=[CH:48][C:47]([C@@H:50]([O:53][Si:54]([C:57]([CH3:58])([CH3:60])[CH3:59])([CH3:56])[CH3:55])[CH2:51][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([C@@H:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:21][CH2:22][N:23]([CH:27]([CH3:28])[CH3:29])[CH:24]([CH3:26])[CH3:25])[CH:14]=2)=[CH:46][C:45]=1[NH:61][S:62]([CH3:65])(=[O:63])=[O:64])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579332174-{4-[(6-Aminohexyl)oxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

Product 2

HCID 222AmmoniaHCID 57933222N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

4-{4-[(6-Aminohexyl)oxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 26, 153 mg, 0.32 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 155 mg, 0.32 mmol), potassium iodide (10 mg) and sodium hydrogen carbonate (104 mg, 1.23 mmol) were heated in propionitrile (3 ml) at 90° C. for 24 hours. The reaction was cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (30 ml), washed with aqueous saturated sodium hydrogen carbonate (30 ml), water (30 ml), brine (30 ml) and dried (magnesium sulphate). The solvent was removed in vacuo and the oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (8511511.5 by volume) to furnish the title compound as a yellow oil, 130 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  3. washwashed with aqueous saturated sodium hydrogen carbonate (30 ml), water (30 ml), brine (30 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customThe solvent was removed in vacuo
  6. customthe oil was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-c99e7ef52d6b43f89f65d28af6388db9
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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