Ammonium formate → N-{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]-2-hydroxyphenyl}formamide

HRID 1433280Notes

Reaction equation

HRID 1433280 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[NH:67][CH:68]=[O:69])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[Si:60]([O:59][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:67][CH:68]=[O:69])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][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:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:44][CH2:45][N:46]([CH:47]([CH3:49])[CH3:48])[CH:50]([CH3:52])[CH3:51])[CH:30]=2)=[CH:22][CH:21]=1)([C:63]([CH3:66])([CH3:64])[CH3:65])([CH3:62])[CH3:61]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933175N-{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}formamide

Product 1

HCID 57933190N-{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]-2-hydroxyphenyl}formamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

N-{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}formamide (Preparation 45, 174 mg, 0.18 mmol) was dissolved in methanol (20 ml) and ammonium formate (230 mg, 3.7 mmol) and 20% palladium hydroxide on carbon (26 mg) added. The stirred reaction was then heated at 90° C. for 2 hours. After cooling to room temperature, the 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, 180 mg.

Workup

  1. customThe stirred reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationthe mixture 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-2a4c6a4b364d48fb8fb723581a84f633
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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