Water → Ammonia

HRID 1433307Notes

Reaction equation

[Si]([O:8][C@H:9]([C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([CH2:55][OH:56])[CH:49]=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.O.[F-].[NH4+]>CO>[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]([OH:8])[C:48]3[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([CH2:55][OH:56])[CH:49]=3)=[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

Conditions

Temperature: 40 °C

Procedure

4-[(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-(hydroxymethyl)phenol (Preparation 63, 311 mg, 0.356 mmol) was dissolved in methanol (4 ml) and water (0.5 ml) and ammonium fluoride (132 mg, 3.56 mmol) was added. The reaction was heated to 40° C. and stirred overnight. Reaction mixture was cooled and solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 90/10/1.0 by volume) to furnish the title compound as a glass, 84 mg.

Workup

customReaction mixture
temperaturewas cooled
customsolvent removed in vacuo
customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record: ord-f482fe72229e48f683164588595ac071
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612084B2

Reaction notes

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