Lithium hydroxide, monohydrate → HCID 10201122, compound

HRID 901851Notes

Reaction equation

HRID 901851 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][C@H:22]([O:28][CH2:29][CH3:30])[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:31]=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][C@H:22]([O:28][CH2:29][CH3:30])[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)[CH2:9][CH2:8][O:7][C:6]=2[CH:31]=1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10224630HCID 10224630, compound

Product 1

HCID 10201122HCID 10201122, compoundYield 94.4%

Procedure

(S)-Ethyl 3-[4-{3-(7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)propylamino}phenyl]-2-ethoxypropanoate (1.7 g, 1 eq, 3.95 mmol) obtained in example 45, was hydrolyzed using lithium hydroxide monohydrate (249 mg, 1.5 eq, 5.93 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 chromatographed using ethyl acetate and hexanes→methanol and chloroform to afford the title compound (1.5 g, yield 94%) 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
  6. customThe residue was chromatographed

Sources & evidence

ORD record
ord-379843aba9364a8a9183fee64d4c15b4
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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