N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433305Notes

Reaction equation

HRID 1433305 reaction equation
[Si]([O:8][C@H:9]([C:43]1[CH:44]=[CH:45][C:46]([OH:54])=[C:47]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:48]=1)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C@@H:27]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH:21]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>O1CCCC1>[NH3:11].[CH:34]([N:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH2:28][C@@H:27]([C:22]1[CH:21]=[C:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:43]2[CH:44]=[CH:45][C:46]([OH:54])=[C:47]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:48]=2)[OH:8])[CH:25]=[CH:24][C:23]=1[OH:26])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933180N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

Product 2

HCID 222AmmoniaHCID 57933231N-(5-{(1R)-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide (Preparation 55, 74 mg, 0.095 mmol) was dissolved in tetrahydrofuran (3 ml) and triethylaminetrihydrofluoride (90 ul, 0.54 mmol) was added in one portion at room temperature. The reaction was stirred for 12 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. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97/3/0.3 to 85/15/1.5 by volume) to furnish the title compound as a yellow solid, 34 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. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-3bbe191e10e3474b8e2d0decd2d35f50
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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