Hydrochloric Acid → HCID 22609613, compound

HRID 2306786Notes

Reaction equation

HRID 2306786 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([N:11](C(OC(C)(C)C)=O)[CH2:12][CH2:13][N:14]2C(OC(C)(C)C)=O)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[C:9](=[O:32])[CH:10]2[CH:15]([NH:14][CH2:13][CH2:12][NH:11]2)[C:16]1=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22609565HCID 22609565, compound

Product 1

HCID 22609613HCID 22609613, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 650 mg (1.5 mmol) of 8-benzyl-2,5-bis-tert-butoxycarbonyl-2,5,8-triazabicyclo-[4,3,0]nonane-7,9-dione in tetrahydrofuran (10 ml) was added 4N hydrogen chloride solution in ethyl acetate (10 ml) with stirring. After 30 minutes at 50° C., a 2.5N aqueous solution of sodium hydroxide (17 ml) was added to the reaction mixture, and the mixture was extracted with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 85 mg (yield: 24%) of 8-benzyl-2,5,8-triazabicyclo[4,3,0]nonane-7,9-dione as a colorless oil.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b90df66ece344ab9699077087d07934
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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