Ammonium formate → Ammonia

HRID 1433287Notes

Reaction equation

HRID 1433287 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][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:11][C:10]=1[NH:57][S:58]([CH3:61])(=[O:60])=[O:59])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:17].[Si:50]([O:49][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:57][S:58]([CH3:61])(=[O:59])=[O:60])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C@@H:33]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:34][CH2:35][N:36]([CH:40]([CH3:42])[CH3:41])[CH:37]([CH3:39])[CH3:38])[CH:27]=1)([C:53]([CH3:56])([CH3:54])[CH3:55])([CH3:52])[CH3:51]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57933228N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}phenyl]methanesulfonamide

Product 2

HCID 222AmmoniaHCID 57933180N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

N-[2-(benzyloxy)-5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)amino]ethyl}phenyl]methanesulfonamide (Preparation 54, 90 mg, 0.10 mmol), ammonium formate (130 mg, 2.0 mmol) and 20% palladium hydroxide on carbon (20 mg) were mixed in ethanol (3 ml) and heated to 70° C. overnight. Reaction mixture was then cooled and filtered. The filtrate was collected 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 91/9/0.9 by volume) to furnish the title compound as a gum to furnish the title compound as a glass, 82 mg.

Workup

  1. customReaction mixture
  2. temperaturewas then cooled
  3. filtrationfiltered
  4. customThe filtrate was collected
  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-eab389c8f2e04083a89566dad26bf607
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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