Lithium hydroxide, monohydrate → HCID 10271353, compound

HRID 901842Notes

Reaction equation

HRID 901842 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([O:24][CH2:25][CH3:26])[C:19]([O:21]CC)=[O:20])=[CH:13][CH:12]=2)[C:3]2[CH:27]=[CH:28][CH:29]=[CH:30][C:2]1=2.O.[OH-].[Li+]>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([O:24][CH2:25][CH3:26])[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=2)[C:3]2[CH:27]=[CH:28][CH:29]=[CH:30][C:2]1=2

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10112367HCID 10112367, compound

Product 1

HCID 10271353HCID 10271353, compoundYield 68%

Procedure

Ethyl 3-[4-{3-(3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (700 mg, 0.98 mmol) obtained in example 1, was hydrolyzed using lithium hydroxide monohydrate (123 mg, 2.9 mmol), in methanol-water at RT till all the starting material was consumed (4 to 5 h). The reaction mixture was diluted with water, acidified with dil. HCl to adjust the pH to ˜4-5 and then extracted with ethyl acetate. The ethyl acetate layer was dried over Na2SO4 and concentrated on rotavapour. The residue was chromatographed using methanol and chloroform to yield the title compound as viscous liquid (256 mg, yield 68%).

Workup

  1. customin methanol-water at RT till all the starting material was consumed (4 to 5 h)
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over Na2SO4
  5. concentrationconcentrated on rotavapour
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-adefdd024a8d400e80403b1e48a7dfdc
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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