Methanol → Ammonia

HRID 1433306Notes

Reaction equation

HRID 1433306 reaction equation
[Si]([O:8][C@H:9]([C:49]1[CH:50]=[CH:51][C:52]([OH:60])=[C:53]([NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[CH:54]=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][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C@@H:33]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:34][CH2:35][N:36]([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])[CH:27]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CO.CCN(CC)CC.F.F.F>O1CCCC1>[NH3:11].[CH:40]([N:36]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH2:34][C@@H:33]([C:28]1[CH:27]=[C:26]([CH2:25][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:49]3[CH:50]=[CH:51][C:52]([OH:60])=[C:53]([NH:55][S:56]([CH3:59])(=[O:58])=[O:57])[CH:54]=3)[OH:8])=[CH:15][CH:16]=2)[CH:31]=[CH:30][C:29]=1[OH:32])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)([CH3:42])[CH3:41]

Participants

6

Reactant 3

HCID 887MethanolHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933219HCID 57933219, compound

Product 2

HCID 222AmmoniaHCID 57933215HCID 57933215, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide (Preparation 61, 250 mg, 0.29 mmol) was dissolved in tetrahydrofuran (10 ml) and methanol (0.5 ml) and triethylaminetrihydrofluoride (1.0 ml, 6.1 mmol) was added. The reaction was stirred for 3 days and the solvent removed in vacuo. The residue was dissolved in 880 ammonia (1 ml) and the solvent removed under reduced pressure, this was repeated 3 times. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 by volume) to furnish the title compound as a pale yellow foam, 100 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in 880 ammonia (1 ml)
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-53f0b1ad9d124595892a140974ba3024
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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