Potassium Iodide → Ammonia

HRID 1433275Notes

Reaction equation

HRID 1433275 reaction equation
[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]

Participants

9

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c5aa7cf2590f4829b357376bd55dca1c
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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