Sodium Bicarbonate → HCID 67992384, compound

HRID 1803378Notes

Reaction equation

HRID 1803378 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:24]=[C:23]1[CH2:35]Cl)[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C1COCC1>[CH:32]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:33]=1[C:34]1[N:22]3[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[CH2:9][O:8][CH2:35][C:23]3=[N:24][C:25]=1[CH:26]=[N:27]2

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86619536HCID 86619536, compound

Product 1

HCID 67992384HCID 67992384, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl (4S)-5-{[tert-butyl(dimethyl)silyl]oxy}-4-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentylcarbamate (1.28 g, 2.40 mmol) was dissolved in 200 mL of CH2Cl2 and the solution was cooled to −78° C. under N2. A 1.0 M solution of tetrabutylammonium fluoride in THF (2.88 mL) was added and the reaction mixture was allowed to warm to ambient temperature. After 4 days, the reaction mixture was then treated with 50 mL of saturated sodium bicarbonate solution. The layers were separated and the organic portion was washed with H2O (50 mL) and brine (4×25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 4% methanol/CHCl3) gave tert-butyl 3-[(11S)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propylcarbamate (820 mg) as a light yellow foam.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe layers were separated
  3. washthe organic portion was washed with H2O (50 mL) and brine (4×25 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc1d9cc849054f08b807fa326dab76ef
Source dataset
uspto-grants-2013_01
Patent number
US08350034B2

Reaction notes

Loading…