Biphenyl-2-ylcarbamic Acid 1-(9-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]amino}nonyl)-piperidin-4-yl Ester → HCID 66967735, compound

HRID 2252103Notes

Reaction equation

HRID 2252103 reaction equation
C([N:8]([CH2:40][C@@H:41]([C:50]1[CH:59]=[CH:58][C:57]([O:60]CC2C=CC=CC=2)=[C:56]2[C:51]=1[CH:52]=[CH:53][C:54](=[O:68])[NH:55]2)[O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:20][CH2:19]1)C1C=CC=CC=1>CO>[Si:43]([O:42][C@H:41]([C:50]1[CH:59]=[CH:58][C:57]([OH:60])=[C:56]2[C:51]=1[CH:52]=[CH:53][C:54](=[O:68])[NH:55]2)[CH2:40][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH:21]([O:24][C:25](=[O:39])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:22][CH2:23]1)([C:46]([CH3:49])([CH3:47])[CH3:48])([CH3:45])[CH3:44]

Participants

3

Reactant 1

HCID 86600266Biphenyl-2-ylcarbamic Acid 1-(9-{Benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethyl]amino}nonyl)-piperidin-4-yl Ester

Product 1

HCID 66967735HCID 66967735, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 500-mL round-bottomed flask was added a sample of the crude solution of biphenyl-2-yl-carbamic acid 1-(9-{benzyl-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydro-quinolin-5-yl)-2-(tert-butyldimethyl-silanyloxy)ethyl]amino}nonyl)piperidin-4-yl ester (50 mL containing about 17.5 g, 18.5 mmol) and methanol (150 mL) and the resulting mixture was stirred until homogeneous (if necessary, any undissolved solids can be removed by filtration through a pad of Celite). The flask was then purged with hydrogen gas for 5 minutes and then palladium hydroxide (3.5 g, 20% Pd (dry basis) on carbon, 60% water) was added. The resulting mixture was stirred at room temperature while hydrogen gas was slowly bubbled through the mixture for about 5 hours (>98% conversion by HPLC). The reaction mixture was then filtered through a pad of Celite and the solvent was removed under reduced pressure to give crude biphenyl-2-yl-carbamic acid 1-{9-[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]nonyl}piperidin-4-yl ester as a yellow solid (16 g).

Workup

  1. customcan be removed by filtration through a pad of Celite)
  2. customThe flask was then purged with hydrogen gas for 5 minutes
  3. additionpalladium hydroxide (3.5 g, 20% Pd (dry basis) on carbon, 60% water) was added
  4. stirringThe resulting mixture was stirred at room temperature while hydrogen gas
  5. customwas slowly bubbled through the mixture for about 5 hours (>98% conversion by HPLC)
  6. filtrationThe reaction mixture was then filtered through a pad of Celite
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-95d792a09a5b4a91adff20df680e78d5
Source dataset
uspto-grants-2008_01
Patent number
US07320990B2

Reaction notes

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