Hydrochloric Acid → HCID 10180845, compound

HRID 901844Notes

Reaction equation

HRID 901844 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:28])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([O:25][CH2:26][CH3:27])[C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=2)[C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2.O.[OH-].[Li+].Cl>CO.O.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:28])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]([O:25][CH2:26][CH3:27])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)[C:3]2[CH:29]=[CH:30][CH:31]=[CH:32][C:2]1=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 10225269HCID 10225269, compound

Product 1

HCID 10180845HCID 10180845, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Methyl 3-[4-{5-(3,4-dihydro-2H-benzo[b][1,4]oxazin-4-yl)-5-oxopentylamino}phenyl]-2-ethoxypropanoate (211 mg, 1 eq, 0.48 mmol) obtained in example 10, was hydrolyzed using lithium hydroxide monohydrate (60 mg, 3 eq, 1.44 mmol) in methanol-water at RT (takes 4-5 h). The reaction mixture was diluted with water, acidified (pH 3-4) with aqueous 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 (ethyl acetate and hexane→methanol/chloroform) to afford the title compound (139 mg, yield 68%) as viscous liquid.

Workup

  1. customat RT
  2. custom(takes 4-5 h)
  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 (ethyl acetate and hexane→methanol/chloroform)

Sources & evidence

ORD record
ord-bebf94be42114c95b4e916c27b378d97
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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