Lithium hydroxide, monohydrate → HCID 10134629, compound

HRID 901846Notes

Reaction equation

HRID 901846 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:12]=[C:13]([CH2:17][CH:18]([O:23][CH2:24][CH3:25])[C:19]([O:21]C)=[O:20])[CH:14]=[CH:15][CH:16]=2)[C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][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:12]=[C:13]([CH2:17][CH:18]([O:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20])[CH:14]=[CH:15][CH:16]=2)[C:3]2[CH:26]=[CH:27][CH:28]=[CH:29][C:2]1=2

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59700566HCID 59700566, compound

Product 1

HCID 10134629HCID 10134629, compoundYield 61%

Procedure

Methyl 3-[3-{3-(3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (350 mg, 1 eq, 0.87 mmol) obtained in example 13, was hydrolyzed using lithium hydroxide monohydrate (110 mg, 3 eq, 2.64 mmol), in methanol-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 chromatographed using methanol and chloroform to afford the title compound (203 mg, yield 61%) as viscous oil.

Workup

  1. customin methanol-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
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-e185984ec4094298b5ae23d1aba5ca21
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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