Hydrochloric Acid → HCID 10447209, compound

HRID 1354388Notes

Reaction equation

HRID 1354388 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:20])[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].[OH-].[Li+].Cl>O1CCCC1>[OH:20][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:10]([NH:9][CH:4]([CH2:5][CH:6]([CH3:8])[CH3:7])[C:3]([OH:22])=[O:2])=[O:21])[CH:18]=[CH:17][C:16]=1[OH:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69420017HCID 69420017, compound

Product 1

HCID 10447209HCID 10447209, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(3,4-dihydroxyphenyl)propionylamino]-4-methyl pentanoic acid methyl ester (200 mg), prepared in Example 13, was dissolved in tetrahydrofuran (5 mL) and treated with 2M lithium hydroxide (1 mL). The resulting mixture was stirred for 18 hours at room temperature. The resulting reaction was neutralized with aqueous hydrochloric acid, extracted with ethylacetate (EtOAc) (100 mL), dried over magnesium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (column size: 25 mm×150 mm, silica gel 70-230 mesh, eluent: hexan/EtOAc (1/5)) to obtain 184.5 mg of the title compound. The yield was 97%. The results of analyses of the compound are as follows:

Workup

  1. customThe resulting reaction
  2. extractionextracted with ethylacetate (EtOAc) (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography (column size: 25 mm×150 mm, silica gel 70-230 mesh, eluent: hexan/EtOAc (1/5))

Sources & evidence

ORD record
ord-250112b6d30b4d669aba02d048a95f3a
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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