HCID 86646974, compound → HCID 86646975, compound

HRID 1468545Notes

Reaction equation

HRID 1468545 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:72][Si:73]([C:76]([CH3:79])([CH3:78])[CH3:77])([CH3:75])[CH3:74])[CH2:21][NH:22][C@H:23]([CH3:71])[CH2:24][C:25]2[CH:26]=[C:27]([CH2:31][CH2:32][NH:33][C:34]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([CH2:43][NH:44][C:45]([CH2:47][CH2:48][N:49]4[CH2:54][CH2:53][CH:52]([O:55][C:56](=[O:70])[NH:57][C:58]5[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=5[C:64]5[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=5)[CH2:51][CH2:50]4)=[O:46])=[CH:39][CH:38]=3)=[O:35])[CH:28]=[CH:29][CH:30]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CCO.[Pd]>[Si:73]([O:72][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][C@H:23]([CH3:71])[CH2:24][C:25]1[CH:26]=[C:27]([CH2:31][CH2:32][NH:33][C:34]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([CH2:43][NH:44][C:45]([CH2:47][CH2:48][N:49]3[CH2:50][CH2:51][CH:52]([O:55][C:56](=[O:70])[NH:57][C:58]4[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=4[C:64]4[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=4)[CH2:53][CH2:54]3)=[O:46])=[CH:41][CH:42]=2)=[O:35])[CH:28]=[CH:29][CH:30]=1)([C:76]([CH3:77])([CH3:78])[CH3:79])([CH3:74])[CH3:75]

Participants

4

Reactant 1

HCID 86646974HCID 86646974, compound

Product 1

HCID 86646975HCID 86646975, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dry nitrogen was bubbled into a stirred solution of biphenyl-2-ylcarbamic acid 1-{2-[(4-{[2-(3-{(R)-2-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)-ethylamino]propyl}phenyl)ethylcarbamoyl]-methyl}phenyl)methylcarbamoyl]ethyl}-piperidin-4-yl ester (0.704 g, 0.650 mmol) in EtOH (5.00 mL) for 3 min and then palladium on carbon (10 wt. %, ˜50% water; 0.289 g, 0.130 mmol) was added. Hydrogen was bubbled into the reaction mixture for 3 min and then the mixture was stirred under an atmosphere of hydrogen (balloon) for 1 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give the title compound, which was used without further purification in the next reaction.

Workup

  1. customHydrogen was bubbled into the reaction mixture for 3 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58806ffa5a9e4e66a210004f82e4be90
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

Loading…