HCID 86619527, compound → HCID 86619528, compound

HRID 1663426Notes

Reaction equation

HRID 1663426 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][C:22]=1[N+:31]([O-])=O)[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[Pt]>[NH2:31][C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[NH:20][C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

4

Reactant 1

HCID 86619527HCID 86619527, compound

Product 1

HCID 86619528HCID 86619528, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

tert-Butyl (2S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-[(3-nitroquinolin-4-yl)amino]propylcarbamate (4.84 g, 10.1 mmol) was dissolved in 150 mL of toluene and the solution was placed in a pressure bottle. Platinum on carbon (5%, 680 mg) was then added and the reaction mixture was shaken under H2 at 52 PSI (3.6×105 Pa). After 8 hours, the reaction mixture was then filtered through a pad of CELITE filter agent. The pad was rinsed with 2-propanol and the combined filtrates were concentrated under reduced pressure to give tert-butyl (2S)-2-[(3-aminoquinolin-4-yl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}propylcarbamate (4.51 g) as a brown foam.

Workup

  1. filtrationthe reaction mixture was then filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with 2-propanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-40f9e9b4492445ab85952f8430e20798
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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