N,N-Diethylethanamine trihydrofluoride → N-{5-[(1R)-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide

HRID 1433295Notes

Reaction equation

HRID 1433295 reaction equation
[Si]([O:8][C@H:9]([C:47]1[CH:48]=[CH:49][C:50]([OH:58])=[C:51]([NH:53][S:54]([CH3:57])(=[O:56])=[O:55])[CH:52]=1)[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C@@H:31]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:32][CH2:33][N:34]([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])[CH:25]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>O1CCCC1.CO>[CH:38]([N:34]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:32][C@@H:31]([C:26]1[CH:25]=[C:24]([CH2:23][CH2:22][CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:47]3[CH:48]=[CH:49][C:50]([OH:58])=[C:51]([NH:53][S:54]([CH3:57])(=[O:56])=[O:55])[CH:52]=3)[OH:8])=[CH:15][CH:16]=2)[CH:29]=[CH:28][C:27]=1[OH:30])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([CH3:39])[CH3:40]

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933188N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide

Product 1

HCID 57933213N-{5-[(1R)-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide (Preparation 10, 98 mg, 0.11 mmol) was dissolved in tetrahydrofuran (4 ml) and methanol (2 ml) and triethylaminetrihydrofluoride (95 ul, 0.58 mmol) was added in one portion at room temperature. The reaction was stirred for 24 hours and the solvent removed under reduced pressure, the residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure to yield an off white solid. The solid was dissolved in methanol (1 ml) and precipitated with an excess of diisopropylether, the solid was collected by filtration to furnish the title compound as a white solid, 16 mg.

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (10 ml)
  3. custom880 ammonia (1 ml) and the solvent removed under reduced pressure
  4. customto yield an off white solid
  5. customprecipitated with an excess of diisopropylether
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-359fb0c673d0469a86da5937b021a56f
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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