Hydrochloric Acid → HCID 131726342, compound

HRID 1820640Notes

Reaction equation

HRID 1820640 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH:5]2[C:9]3([CH2:18][C:19]4[C:24]([N:4]2[C:3]1=[O:33])=[CH:23][CH:22]=[C:21]([NH:25]C(=O)OC(C)(C)C)[CH:20]=4)[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]3=[O:17].[ClH:34].O1CCOCC1>C(Cl)Cl>[ClH:34].[NH2:25][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:4]1[C:3](=[O:33])[CH:2]([CH3:1])[O:7][CH:6]([CH3:8])[CH:5]1[C:9]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]1=[O:17])[CH2:18]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131726344HCID 131726344, compound

Product 1

HCID 131726342HCID 131726342, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of tert-butyl 1,1′,2,3′,4,4′,4a,6′-octahydro-2,4-dimethyl-2′,4′,6′-trioxospiro[[1,4]oxazino[4,3-a]quinolone-5(6H),5′(2′H)-pyrimidin]-8-ylcarbamate (from Example 15) (7.4 g, 16.65 mmoles) in 250 mL of CH2Cl2 at room temperature is treated via pipette with a solution of 4.0 N HCl in dioxane (20 mL, 80 mmoles). The resulting slurry is stirred at room temperature for 2 days and then concentrated. The residue is dissolved in hot 1:1 EtOAc/methanol (˜300 mL) and recrystallized from heptane. After cooling to room temperature and then stirring at 0° C. for 30 minutes, the solid is isolated by filtration and dried (20 torr, 60° C., for 18 h) to give 6.31 g (99%) of the title compound as a beige solid. 1H NMR (DMSO-d6): δ 11.78, 11.47, 9.83, 7.06, 6.92, 6.87, 4.03, 3.67, 3.60, 3.50, 3.41, 2.90-2.82, 1.13, 0.91.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in hot 1:1 EtOAc/methanol (˜300 mL)
  3. customrecrystallized from heptane
  4. temperatureAfter cooling to room temperature
  5. stirringstirring at 0° C. for 30 minutes
  6. customthe solid is isolated by filtration
  7. customdried (20 torr, 60° C., for 18 h)

Sources & evidence

ORD record
ord-05d70120ed3a4943aebfbb3c1ec7718a
Source dataset
uspto-grants-2009_10
Patent number
US07605157B2

Reaction notes

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