Hydrochloric Acid → HCID 67089765, compound

HRID 2378726Notes

Reaction equation

HRID 2378726 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:25]=[CH:24][C:15]([C:16]([NH:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:17])=[CH:14][CH:13]=2)=[N:2]1.[OH-].[Na+].Cl>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])=[CH:24][CH:25]=2)=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86612729HCID 86612729, compound

Product 1

HCID 67089765HCID 67089765, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Compound 52 (1.65 g, 4.93 mmol) was dissolved in THF (30 mL), then the solution was added with 2 mol/L aqueous sodium hydroxide solution (15.0 mL) at 0° C., followed by stirring at 70° C. for 1 hour. The reaction mixture was neutralized with 2 mol/L hydrochloric acid, then was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and was concentrated. The residue was recrystallized from ethyl acetate and methanol to obtain Compound 53 (662 mg, 42%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationwas concentrated
  4. customThe residue was recrystallized from ethyl acetate and methanol

Sources & evidence

ORD record
ord-b1ca9b5f433949e9969998f675a83b91
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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