Biphenyl-2-ylcarbamic Acid 1-[2-({3-[4-(2-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]-amino}ethyl)phenylcarbamoyl]phenyl}methylcarbamoyl)ethyl]piperidin-4-yl Ester → Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-{2-[(R)-2-(tert-Butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]ethyl}phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl Ester

HRID 1055342Notes

Reaction equation

HRID 1055342 reaction equation
C([N:8]([CH2:54][C@@H:55]([C:64]1[CH:73]=[CH:72][C:71]([O:74]CC2C=CC=CC=2)=[C:70]2[C:65]=1[CH:66]=[CH:67][C:68](=[O:82])[NH:69]2)[O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[CH:21]=[C:22]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([O:38][C:39](=[O:53])[NH:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:34][CH2:33]3)=[O:29])[CH:23]=[CH:24][CH:25]=2)=[O:19])=[CH:13][CH:12]=1)C1C=CC=CC=1>CCO.CC(O)=O.[Pd]>[Si:57]([O:56][C@H:55]([C:64]1[CH:73]=[CH:72][C:71]([OH:74])=[C:70]2[C:65]=1[CH:66]=[CH:67][C:68](=[O:82])[NH:69]2)[CH2:54][NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]([C:20]2[CH:21]=[C:22]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH:35]([O:38][C:39](=[O:53])[NH:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:34][CH2:33]3)=[O:29])[CH:23]=[CH:24][CH:25]=2)=[O:19])=[CH:15][CH:16]=1)([C:60]([CH3:63])([CH3:61])[CH3:62])([CH3:59])[CH3:58]

Participants

5

Reactant 1

HCID 86646971Biphenyl-2-ylcarbamic Acid 1-[2-({3-[4-(2-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]-amino}ethyl)phenylcarbamoyl]phenyl}methylcarbamoyl)ethyl]piperidin-4-yl Ester

Product 1

HCID 86646972Biphenyl-2-ylcarbamic Acid 1-(2-{[3-(4-{2-[(R)-2-(tert-Butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]ethyl}phenylcarbamoyl)phenyl]methylcarbamoyl}ethyl)piperidin-4-yl EsterYield 76%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of biphenyl-2-ylcarbamic acid 1-[2-({3-[4-(2-{benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert- butyldimethylsilanyloxy)ethyl]-amino}ethyl)phenylcarbamoyl]phenyl}methylcarbamoyl)ethyl]piperidin-4-yl ester (1.74 g, 1.56 mmol) in EtOH (12.2 mL) and AcOH (0.122 mL) was flushed with nitrogen for 3 min. Palladium on carbon (10%, ˜50% water, 0.18 g) was added and the reaction mixture was flushed with hydrogen for 4 min. The mixture was stirred under a hydrogen atmosphere (balloon) overnight and then filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-15% MeOH in DCM) to give the title compound (1.11 g, 76% yield) as a thick brownish liquid.

Workup

  1. customthe reaction mixture was flushed with hydrogen for 4 min
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel flash chromatography (0-15% MeOH in DCM)

Sources & evidence

ORD record
ord-971954e45d064c7b9d68a20e1909ed36
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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