Ammonium formate → N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

HRID 1433255Notes

Reaction equation

HRID 1433255 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([O:32]CC3C=CC=CC=3)=[C:28]([C@@H:40]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[CH2:41][CH2:42][N:43]([CH:47]([CH3:49])[CH3:48])[CH:44]([CH3:46])[CH3:45])[CH:27]=2)=[CH:11][C:10]=1[NH:64][S:65]([CH3:68])(=[O:67])=[O:66])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[Si:57]([O:56][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:64][S:65]([CH3:68])(=[O:66])=[O:67])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([C@@H:40]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH2:41][CH2:42][N:43]([CH:47]([CH3:49])[CH3:48])[CH:44]([CH3:46])[CH3:45])[CH:27]=1)([C:60]([CH3:63])([CH3:61])[CH3:62])([CH3:59])[CH3:58]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933197N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide

Product 1

HCID 57933236N-(5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[(7-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenoxy}heptyl)amino]ethyl}-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

N-{2-(Benzyloxy)-5-[(1R)-2-[(7-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenoxy}heptyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Preparation 19, 96 mg, 0.10 mmol) and palladium hydroxide (20% by weight on carbon, 25 mg, 0.04 mmol) were dissolved in ethanol (3 ml), then ammonium formate (69 mg, 1.1 mmol) was added and heated to 80° C. for 1 hour. The reaction was cooled to room temperature and the mixture was filtered through Arbocel™ and the solvent removed in vacuo. The residue was dissolved in dichloromethane (containing a trace of methanol) and washed with water (brine was added to aid in the separation), the organic layer was dried (magnesium sulphate), filtered, and the solvents removed in vacuo to yield the title compound as a white foam, 68 mg.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe mixture was filtered through Arbocel™
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (
  5. additioncontaining a trace of methanol) and
  6. washwashed with water (brine
  7. additionwas added to aid in the separation), the organic layer
  8. dry with materialwas dried (magnesium sulphate)
  9. filtrationfiltered
  10. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-1b69515de63e48fa9fc7a101d18a9f62
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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