N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433299Notes

Reaction equation

HRID 1433299 reaction equation
[Si]([O:8][C@H:9]([C:46]1[CH:47]=[CH:48][C:49]([OH:57])=[C:50]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:51]=1)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C@@H:30]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:24]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>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][CH2:20][CH2:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:46]2[CH:47]=[CH:48][C:49]([OH:57])=[C:50]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:51]=2)[OH:8])[CH:28]=[CH:27][C:26]=1[OH:29])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38]

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933211N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]-2-hydroxyphenyl}methanesulfonamide

Product 2

HCID 222AmmoniaHCID 54582151N-(5-((R)-2-(6-(4-(3-((R)-3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)butoxy)hexylamino)-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]-2-hydroxyphenyl}methanesulfonamide (Preparation 28, 420 mg, 0.51 mmol) was dissolved in tetrahydrofuran (6 ml) and triethylaminetrihydrofluoride (415 ul, 2.55 mmol) was added. The reaction was stirred at room temperature for 4 hours and the solvent removed in vacuo, the residue was dissolved in methanol (1 ml) and 880 ammonia (1 ml) and the solvent removed in vacuo, the residue was dissolved in methanol (1 ml) and 880 ammonia (1 ml) and the solvent removed in vacuo. The resulting oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (89/11/1.1 by volume) to furnish the title compound as a yellow solid, 26 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (1 ml)
  3. custom880 ammonia (1 ml) and the solvent removed in vacuo
  4. dissolutionthe residue was dissolved in methanol (1 ml)
  5. custom880 ammonia (1 ml) and the solvent removed in vacuo
  6. customThe resulting oil was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3b51118523724995ac2c42c9de886b94
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

Loading…