Hydrochloric Acid → HCID 10064160, compound

HRID 1354386Notes

Reaction equation

HRID 1354386 reaction equation
C[O:2][C:3](=[O:24])[CH:4]([NH:12][C:13](=[O:23])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Li+].Cl>O1CCCC1>[OH:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][C:13]([NH:12][CH:4]([CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:3]([OH:24])=[O:2])=[O:23])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 9996544HCID 9996544, compound

Product 1

HCID 10064160HCID 10064160, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(4-hydroxyphenyl)propionylamino]-3-phenyl propionic acid methyl ester (200 mg), prepared in Example 4, 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 150 mg of the title compound. The yield was 78%. 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-1962dd6ce96545d5981d53088612f3ea
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

Loading…