Lithium hydroxide, monohydrate → HCID 10136668, compound

HRID 901854Notes

Reaction equation

HRID 901854 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[N:4]([CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([O:30][CH2:31][CH3:32])[C:25]([O:27]CC)=[O:26])=[CH:19][CH:18]=2)[CH2:3]1.O.[OH-].[Li+]>>[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:5]=2[N:4]([CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]([O:30][CH2:31][CH3:32])[C:25]([OH:27])=[O:26])=[CH:21][CH:22]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10182020HCID 10182020, compound

Product 1

HCID 10136668HCID 10136668, compoundYield 64%

Procedure

Ethyl 3-[4-{3-(2-methyl-7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (320 mg, 1 eq, 0.72 mmol) obtained in example 52, was hydrolyzed using lithium hydroxide monohydrate (46 mg, 1.5 eq, 1.08 mmol), in methanol-THF-water at RT till all the starting material is consumed (4 to 5 h). The reaction mixture was diluted with water, acidified (pH ˜4-5) with dil. HCl and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated on rotary evaporator. The residue was chromatoghaphed using methanol and chloroform to afford the title compound (190 mg, yield 64%) as viscous liquid.

Workup

  1. customin methanol-THF-water at RT till all the starting material is 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 anhydrous sodium sulfate
  5. concentrationconcentrated on rotary evaporator

Sources & evidence

ORD record
ord-c1c92f706d564efdb1c3f74357b09291
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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