Hydrochloric Acid → 2-[3-(4-Hydroxyphenyl)propionylamino]-3-methyl butyric acid

HRID 1354387Notes

Reaction equation

HRID 1354387 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[CH:5]([CH3:7])[CH3:6].[OH-].[Li+].Cl>O1CCCC1>[OH:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]([NH:8][CH:4]([CH:5]([CH3:7])[CH3:6])[C:3]([OH:20])=[O:2])=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 117783682-[3-(4-Hydroxyphenyl)propionylamino]-3-methyl butyric acid methyl ester

Product 1

HCID 103781812-[3-(4-Hydroxyphenyl)propionylamino]-3-methyl butyric acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(4-hydroxyphenyl)propionylamino]-3-methyl butyric acid methyl ester (200 mg), prepared in Example 9, was dissolved in tetrahydrofuran (10 mL) and treated with 2M lithium hydroxide (1 mL). The resulting mixture was stirred for 18 hours at room temperature. The 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: EtOAc) to obtain 160 mg of the title compound. The yield was 84%. The results of analyses of the compound are as follows:

Workup

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

Sources & evidence

ORD record
ord-b3ee0ca01fff4b49ac6a31179b2b7904
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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