N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433303Notes

Reaction equation

HRID 1433303 reaction equation
[Si]([O:8][C@H:9]([C:46]1[CH:47]=[CH:48][C:49]([OH:55])=[C:50]([NH:52][CH:53]=[O:54])[CH:51]=1)[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C@@H:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:24]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>CO.O1CCCC1>[NH3:11].[CH:37]([N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][C@@H:30]([C:25]1[CH:24]=[C: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:46]3[CH:47]=[CH:48][C:49]([OH:55])=[C:50]([NH:52][CH:53]=[O:54])[CH:51]=3)[OH:8])=[CH:15][CH:16]=2)[CH:28]=[CH:27][C:26]=1[OH:29])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:38])[CH3:39]

Participants

6

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933190N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide

Product 2

HCID 222AmmoniaHCID 57933198N-{5-[(1R)-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}formamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide (Preparation 46, 180 mg, 0.18 mmol) was dissolved in methanol (5 ml) and tetrahydrofuran (10 ml), and triethylaminetrihydrofluoride (0.18 ml, 1.1 mmol) added. The mixture was stirred overnight and then the solvent removed in vacuo. The residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure. This was repeated and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98/2/0.2 to 80/20/2.0 by volume) to furnish the title compound as a gum, 69 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in methanol (10 ml)
  3. custom880 ammonia (1 ml) and the solvent removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-1cad7a13285f4e9fb93ff90082773a62
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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