Ethyl Acetate → Ammonia

HRID 1433286Notes

Reaction equation

HRID 1433286 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:11]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:53])[CH3:52])[CH2:48]Br)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CS(C)=O>[NH3:1].[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([O:50][Si:51]([C:54]([CH3:55])([CH3:57])[CH3:56])([CH3:53])[CH3:52])[CH2:48][NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([C@@H:17]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:18][CH2:19][N:20]([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:25])[CH3:26])[CH:11]=2)=[CH:43][C:42]=1[NH:58][S:59]([CH3:62])(=[O:60])=[O:61])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 579331874-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

Product 2

HCID 222AmmoniaHCID 57933228N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-(8-aminooctyl)-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 53, 170 mg, 0.39 mmol) and N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 191 mg, 0.37 mmol) were heated at 90° C. in dimethylsulfoxide (0.5 ml) overnight. Ethyl acetate and saturated aqueous sodium hydrogen carbonate were added and the organics separated, washed with saturated aqueous sodium hydrogen carbonate, brine, 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 95/5/0.5 by volume) to furnish the title compound as a yellow oil, 90 mg.

Workup

  1. washthe organics separated, washed with saturated aqueous sodium hydrogen carbonate, brine
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-0ab038e0e3824f7ba8fe3aa7a7db2ec1
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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