Ammonia → Ammonia

HRID 1433300Notes

Reaction equation

HRID 1433300 reaction equation
[Si]([O:8][C@H:9]([C:48]1[CH:49]=[CH:50][C:51]([OH:57])=[C:52]([NH:54][CH:55]=[O:56])[CH:53]=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][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([C@@H:32]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:33][CH2:34][N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])[CH:26]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F.N>O1CCCC1>[NH3:11].[CH:39]([N:35]([CH:36]([CH3:38])[CH3:37])[CH2:34][CH2:33][C@@H:32]([C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:48]3[CH:49]=[CH:50][C:51]([OH:57])=[C:52]([NH:54][CH:55]=[O:56])[CH:53]=3)[OH:8])=[CH:19][CH:18]=2)[CH:30]=[CH:29][C:28]=1[OH:31])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([CH3:41])[CH3:40]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933165N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-(3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide

Product 2

HCID 222AmmoniaHCID 57933176N-{5-[(1R)-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}formamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}formamide (Preparation 30, 280 mg, 0.35 mmol) was dissolved in tetrahydrofuran (5 ml) and triethylaminetrihydrofluoride (0.29 ml, 1.8 mmol) was added, and the mixture stirred overnight at room temperature. Tetrahydrofuran (6 ml) and 880 ammonia (6 ml) were then added, the mixture stirred for 20 minutes, organics were then separated and washed with saturated aqueous sodium hydrogen carbonate (10 ml), then brine (10 ml), then 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 (98/2/0.2 to 88/12/1.2 by volume) to furnish the title compound as an off-white solid, 74 mg.

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. customorganics were then separated
  3. washwashed with saturated aqueous sodium hydrogen carbonate (10 ml)
  4. dry with materialbrine (10 ml), then dried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-6b06f31d046a453092d3f1eff784e2bf
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

Loading…