Ammonium formate → 5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]benzene-1,3-diol

HRID 1433278Notes

Reaction equation

HRID 1433278 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][CH2:27][C@@H:28]([C:37]3[CH:42]=[C:41]([O:43]CC4C=CC=CC=4)[CH:40]=[C:39]([O:51]CC4C=CC=CC=4)[CH:38]=3)[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:20][CH:19]=2)=[CH:11][C:10]=1[C@@H:59]([C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[CH2:60][CH2:61][N:62]([CH:66]([CH3:68])[CH3:67])[CH:63]([CH3:65])[CH3:64])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[Si:30]([O:29][C@H:28]([C:37]1[CH:42]=[C:41]([OH:43])[CH:40]=[C:39]([OH:51])[CH:38]=1)[CH2:27][NH:26][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([C@@H:59]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[CH2:60][CH2:61][N:62]([CH:63]([CH3:65])[CH3:64])[CH:66]([CH3:68])[CH3:67])[CH:11]=2)=[CH:19][CH:20]=1)([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933155(3R)-3-[2-(benzyloxy)-5-{2-[4-(2-{[(2R)-2-[3,5-bis(benzyloxy)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]ethyl}phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Product 1

HCID 579331935-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]benzene-1,3-diol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

(3R)-3-[2-(benzyloxy)-5-{2-[4-(2-{[(2R)-2-[3,5-bis(benzyloxy)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]ethyl}phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 43, 346 mg, 0.30 mmol) was dissolved in methanol (30 ml) and ammonium formate (380 mg, 6.1 mmol) and 20% palladium hydroxide on carbon (43 mg) added. The stirred reaction was then heated at 90° C. for 2 hours. After cooling to room temperature, mixture was filtered and solvent removed in vacuo. The residue was then taken up in ethyl acetate (50 ml) and saturated aqueous sodium hydrogen carbonate (50 ml). The organics were separated, washed with brine then dried (magnesium sulphate) and the solvent removed in vacuo to yield the title compound as a yellow glass, 174 mg.

Workup

  1. customThe stirred reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationmixture was filtered
  4. customsolvent removed in vacuo
  5. customThe organics were separated
  6. washwashed with brine
  7. dry with materialthen dried (magnesium sulphate)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8e210af1f8f54eaa8dbbbaf899703d8a
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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