Lithium hydroxide, monohydrate → HCID 90410408, compound

HRID 589032Notes

Reaction equation

HRID 589032 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH:14]([C:17]([O:19]CC)=[O:18])[CH:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:12]4[C:28](=[O:30])[NH:29][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:31])[O:4][N:3]=1.O.[OH-].[Li+]>CO.O.CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH:14]([C:17]([OH:19])=[O:18])[CH:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:12]4[C:28](=[O:30])[NH:29][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:31])[O:4][N:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86299108HCID 86299108, compound

Product 1

HCID 90410408HCID 90410408, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(3,5-dimethylisoxazol-4-yl)-2-oxo-4-phenyl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-5-carboxylate (0.150 g, 0.358 mmol) from Example 23 was dissolved in MeOH (3.0 mL) and lithium hydroxide, monohydrate (0.030 g, 0.72 mmol) dissolved in water (1.0 mL) was added. The reaction mixture was stirred at room temperature for 2 h, diluted with EtOAc and washed with saturated water ammonium chloride, brine, dried over magnesium sulfate and concentrated to give a mixture of the diastereoisomers of the title compound as a solid residue (0.145 g, 100%). LCMS calc. for C21H18N3O5 (M+H)+: m/z=392.1. found: 392.1.

Workup

  1. additionwas added
  2. washwashed with saturated water ammonium chloride, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give

Sources & evidence

ORD record
ord-1552bbf21f37458a8f460ab605b5c9a8
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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