Ammonium formate → N-{5-[(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-hydroxyphenyl}methanesulfonamide

HRID 1433251Notes

Reaction equation

HRID 1433251 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[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][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:62][S:63]([CH3:66])(=[O:65])=[O:64])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[Si:55]([O:54][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:62][S:63]([CH3:66])(=[O:64])=[O:65])[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][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=2)=[CH:24][CH:25]=1)([C:58]([CH3:61])([CH3:59])[CH3:60])([CH3:57])[CH3:56]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933232N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide

Product 1

HCID 57933182N-{5-[(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-hydroxyphenyl}methanesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-{2-(benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]phenyl}methanesulfonamide (Preparation 14, 200 mg, 0.2 mmol), and palladium hydroxide (20% by weight on carbon, 50 mg, 0.07 mmol) were dissolved in ethanol (5 ml), then ammonium formate (74 mg, 1.2 mmol) was added and heated to 80° C. for 5 minutes then stirred at 75° C. for 1 hour. Reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. to yield the title compound as a white foam, 190 mg.

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. filtrationthe mixture was filtered through Arbocel™
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c503d0800c4044b79da53206f2f85f3e
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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