Acetic Anhydride → 3-(2-Benzyloxyethyl)-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

HRID 987080Notes

Reaction equation

HRID 987080 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:21])O[C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:29][CH2:30][CH2:31][NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(=O)C)(=O)C>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH:12]2[CH2:19][CH2:18][CH2:17][CH:16]1[C:15](=[O:20])[N:32]([CH2:31][CH2:30][O:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]2=[O:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5338682-(Benzyloxy)ethanamineHCID 544831212,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester2×

Product 1

HCID 540165673-(2-Benzyloxyethyl)-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,4-Dioxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 2, 1.02 g, 3.52 mmol) was dissolved in dioxane (5 mL), and 2-benzyloxyethylamine (0.50 g, 3.32 mmol) was added from the top. The mixture was stirred at room temperature for 1 hour (hr). Then, acetic anhydride (0.62 mL, 6.64 mmol) was added, and the reaction was refluxed for 5 hours. Dioxane was evaporated, and flash chromatographic purification of the residue (20% EtOAc/hexanes) gave Compound 3 (1.26 g, 90%) as a pale yellow oil: Rf (50% EtOAc/hexanes): 0.80.

Workup

  1. temperaturethe reaction was refluxed for 5 hours
  2. customDioxane was evaporated
  3. customflash chromatographic purification of the residue (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9060e5731c6648acb603173e58bb0f3c
Source dataset
uspto-grants-2003_10
Patent number
US06630472B1

Reaction notes

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