Hydrochloric Acid → HCID 21105782, compound

HRID 1354389Notes

Reaction equation

HRID 1354389 reaction equation
C([O:8][C:9](=[O:35])[CH:10]([NH:22][C:23](=[O:34])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[C:28]([OH:33])[CH:27]=1)[CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])C1C=CC=CC=1.[OH-].[Li+].Cl>O1CCCC1>[OH:33][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][C:23]([NH:22][CH:10]([CH2:11][C:12]([OH:14])=[O:13])[C:9]([OH:35])=[O:8])=[O:34])[CH:31]=[CH:30][C:29]=1[OH:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 53394500HCID 53394500, compound

Product 1

HCID 21105782HCID 21105782, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[3-(3,4-dihydroxyphenyl)propionylamino]-succinic acid dibenzyl ester (12 g), prepared in Example 14, was dissolved in tetrahydrofuran (100 mL) and treated with 2M lithium hydroxide (126 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) (500 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: MC/MeOH (5/95)) to obtain 4.28 g of the title compound. The yield was 57%. The results of analyses of the compound are as follows:

Workup

  1. customThe resulting reaction
  2. extractionextracted with ethylacetate (EtOAc) (500 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: MC/MeOH (5/95))

Sources & evidence

ORD record
ord-dec8c10e8a8b430e800eafbc3182c16f
Source dataset
uspto-grants-2007_05
Patent number
US07223793B2

Reaction notes

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