Ammonia → Ammonia

HRID 1433296Notes

Reaction equation

HRID 1433296 reaction equation
[Si]([O:8][C@H:9]([C:48]1[CH:49]=[CH:50][C:51]([OH:59])=[C:52]([NH:54][S:55]([CH3:58])(=[O:57])=[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.F.F.F.C(N(CC)CC)C.N>O1CCCC1.[Cl-].[Na+].O>[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:18]=[CH:19][C:14]([CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:48]3[CH:49]=[CH:50][C:51]([OH:59])=[C:52]([NH:54][S:55]([CH3:58])(=[O:57])=[O:56])[CH:53]=3)[OH:8])=[CH:15][CH:16]=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

7

Reactant 3

HCID 222AmmoniaHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933182N-{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}methanesulfonamide

Product 2

HCID 222AmmoniaHCID 54583100N-(5-((R)-2-(4-(4-(3-((R)-3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)butoxy)phenethylamino)-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

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}methanesulfonamide (Preparation 15, 190 mg, 0.22 mmol) was dissolved in tetrahydrofuran (5 ml) and N,N-diethylethanamine trihydrofluoride (0.2 ml, 1 mmol) was added dropwise. After 29 hours a mixture of tetrahydrofuran (5 ml) and 880 ammonia (5 ml) were added and after 15 minutes brine was added, the organic layer was separated, dried (magnesium sulphate), filtered, the solvents were removed in vacuo and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (981210.2 to 92/8/0.8 by volume) to furnish the title compound as a white foam, 90 mg.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-c736309ff94843ebb2cf1fedbab0a45f
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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