Sodium Bicarbonate → 5-[(R)-2-{(R)-2-[3-(2-Aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one

HRID 1055348Notes

Reaction equation

HRID 1055348 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C@H:17]([NH:19][CH2:20][C@@H:21]([C:30]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[C:36]3[C:31]=2[CH:32]=[CH:33][C:34](=[O:48])[NH:35]3)[O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH3:18])[CH:11]=1)(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][C@H:17]([NH:19][CH2:20][C@@H:21]([C:30]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[C:36]3[C:31]=2[CH:32]=[CH:33][C:34](=[O:48])[NH:35]3)[O:22][Si:23]([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:25])[CH3:24])[CH3:18])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66781587[2-(3-{(R)-2-[(R)-2-(8-Benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)ethyl]carbamic Acid tert-Butyl Ester

Product 1

HCID 667815115-[(R)-2-{(R)-2-[3-(2-Aminoethyl)phenyl]-1-methylethylamino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

A solution of [2-(3-{(R)-2-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)ethyl]carbamic acid tert-butyl ester (2.8 g) in 20% trifluoroacetic acid in DCM was stirred at room temperature for 3 h. Saturated aqueous sodium bicarbonate solution was added to neutralize the TFA and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification.

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-499fa0fd3df44d14960475f7ab7132de
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

Loading…