Hydrochloric Acid → HCID 11384784, compound

HRID 2220152Notes

Reaction equation

HRID 2220152 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([C:8]2[CH:32]=[CH:31][C:11]([CH2:12][N:13]([C:20]3[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=3)[C:23]([O:25]CC)=[O:24])[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)[S:3]1.[OH-].[Na+].Cl>C(O)C>[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][N:13]([C:20]3[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=3)[C:23]([OH:25])=[O:24])[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:31][CH:32]=2)[S:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 23134794HCID 23134794, compound

Product 1

HCID 11384784HCID 11384784, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution ethyl 3-[N-[4-(2,4-dioxothiazolidin-5-yl)benzyl]-N-pentanoylamino]benzoate (0.73 g) obtained in Example 21f in ethanol (10 ml) was added 1N NaOH aqueous solution (3.5 ml), and the mixture was stirred at room temperature for 3 hrs. Then 1N NaOH aqueous solution (1.0 ml) was added, and the mixture was further stirred at room temperature for 3 hrs. To the reaction mixture was added 1N hydrochloric acid (4.5 ml), and the resultant product was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to ODS column chromatography [water containing 1% acetic acid and acetonitrile (1:1)] to give the title compound (0.51 g) as a powder.

Workup

  1. stirringthe mixture was further stirred at room temperature for 3 hrs
  2. extractionthe resultant product was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e058b184c014b66a6e028c0ba45c10b
Source dataset
uspto-grants-2008_08
Patent number
US07417052B2

Reaction notes

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