Lithium hydroxide, monohydrate → HCID 10201121, compound

HRID 901848Notes

Reaction equation

HRID 901848 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:27][CH2:28][CH3:29])[C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:30]=1.O.[OH-].[Li+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][CH2:13][NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:27][CH2:28][CH3:29])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:30]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10158862HCID 10158862, compound

Product 1

HCID 10201121HCID 10201121, compoundYield 70%

Procedure

Methyl 3-[4-{3-(7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (180 mg, 1 eq, 0.43 mmol) obtained in example 16, was hydrolyzed using lithium hydroxide monohydrate (55 mg, 3 eq, 1.2 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 ethyl acetate and hexanes→methanol and chloroform to afford the title compound (121 mg, yield 70%) as viscous liquid.

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-4e38115acb4a4035b0f0ef0fa6a37c30
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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