{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol → 4-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

HRID 1433283Notes

Reaction equation

HRID 1433283 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35]CC4C=CC=CC=4)=[C:31]([C@@H:43]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH2:44][CH2:45][N:46]([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[CH:30]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[CH2:67][OH:68])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[Si:60]([O:59][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:67][OH:68])[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][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:44][CH2:45][N:46]([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[CH:30]=2)=[CH:24][CH:25]=1)([C:63]([CH3:66])([CH3:64])[CH3:65])([CH3:62])[CH3:61]

Participants

4

Reactant 1

HCID 57933171{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol

Product 1

HCID 579332144-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol (Preparation 48, 280 mg, 0.30 mmol) was dissolved in ethanol (6 ml) and palladium hydroxide (20% by weight on carbon, 14 mg, 0.02 mmol) was added. The reaction was the hydrogenated under 40 psi at room temperature for 18 hours, cooled to room temperature and the reaction filtered through Celite™ and the filtrate solvent removed in vacuo to furnish the title compound as a gum, 235 mg.

Workup

  1. customat room temperature
  2. customfor 18 hours
  3. filtrationthe reaction filtered through Celite™
  4. customthe filtrate solvent removed in vacuo

Sources & evidence

ORD record
ord-68296f679fee4f38af83be7dca9e1c68
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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