HCID 57815337, compound → HCID 57815203, compound

HRID 1510773Notes

Reaction equation

HRID 1510773 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([C@@H:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[N:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][C@H:21]3[OH:41])C(=O)OC(C)(C)C)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1>C(O)C.Cl.C(O)C>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][C@@H:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]4[C:37]5[C:32](=[N:33][CH:34]=[C:35]([O:38][CH3:39])[CH:36]=5)[CH:31]=[CH:30][C:29]4=[O:40])[CH2:22][C@H:21]3[OH:41])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57815337HCID 57815337, compound

Product 1

HCID 57815203HCID 57815203, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21887872Ethanol hydrochlorideSolvent

Procedure

To a solution of 75 mg of tert-butyl (2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)((3R,4R)-3-hydroxy-1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate in 3 mL of ethanol, 3.0 mL of a hydrogen chloride/ethanol solution was added at room temperature. The mixture was stirred at the same temperature for 1 hour, and the solvent was distilled off under reduced pressure. Diethyl ether was added to the resultant residue, and the solid was filtered off. To the solid, chloroform and water were added, and the aqueous layer was separated. The aqueous layer was charged with chloroform and adjusted to pH 12 with a 1 mol/L aqueous sodium hydroxide solution. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 45 mg of 1-(2-((3R,4R)-4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-3-hydroxypiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionDiethyl ether was added to the resultant residue
  3. filtrationthe solid was filtered off
  4. additionTo the solid, chloroform and water were added
  5. customthe aqueous layer was separated
  6. additionThe aqueous layer was charged with chloroform
  7. customThe organic layer was separated
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4014543d8c774dd79a6b56d134c05ced
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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