Ammonium formate → N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide

HRID 1433247Notes

Reaction equation

HRID 1433247 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([C@@H:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:38][CH2:39][N:40]([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42])[CH:31]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:61][S:62]([CH3:65])(=[O:64])=[O:63])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[Si:54]([O:53][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:61][S:62]([CH3:65])(=[O:63])=[O:64])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([C@@H:37]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[CH2:38][CH2:39][N:40]([CH:41]([CH3:43])[CH3:42])[CH:44]([CH3:46])[CH3:45])[CH:31]=2)=[CH:24][CH:25]=1)([C:57]([CH3:60])([CH3:58])[CH3:59])([CH3:56])[CH3:55]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933186N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

Product 1

HCID 57933188N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide (Preparation 9, 100 mg, 0.11 mmol) was dissolved in ethanol (10 ml) and ammonium formate (68 mg, 1.07 mmol) and 10% palladium hydroxide on carbon (20 mg) added. The stirred reaction was heated at 90° C. for 2 hours, cooled to room temperature and filtered through Arbocel™, the filtrate was collected and the solvent removed in vacuo to furnish the title compound as a yellow glass, 98 mg.

Workup

  1. customThe stirred reaction
  2. temperaturecooled to room temperature
  3. filtrationfiltered through Arbocel™
  4. customthe filtrate was collected
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-3e23b2ee6433480ebb3acd9265c1aac5
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

Loading…