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Ammonia → Ammonia

HRID 1433297
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Reaction equation

HRID 1433297 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][O: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.F.F.F.C(N(CC)CC)C.CO.N>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]([CH:25]=[CH:24][C:23]=1[OH:26])[O:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][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)[OH:8])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([CH3:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933236N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

Product 2

HCID 222Ammonia
HCID 57933206
N-(5-{(1R)-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide (Preparation 20, 68 mg, 0.087 mmol) was dissolved in tetrahydrofuran (3 ml) and N,N-diethylethanamine trihydrofluoride (71 μl, 0.43 mmol) was added dropwise. After 18 hours a mixture of methanol (4 ml) and 880 ammonia (8 ml) were added and after 15 minutes the solvent was removed in vacuo. The residue was dissolved in dichloromethane and the solvent removed in vacuo again and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97/310.3 to 88/12/1.2 by volume) to furnish the title compound as a white solid, 30 mg.

Workup

  1. additionwere added and after 15 minutes the solvent
  2. customwas removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customthe solvent removed in vacuo again
  5. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-5e60114b731441e7837b3e6e48e39fd4
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07612084B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes