Citric Acid → Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-4-nitrobutanoate

HRID 1279661Notes

Reaction equation

HRID 1279661 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][C:11](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C.[N+:69]([CH3:72])([O-:71])=[O:70]>>[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH:21]([CH2:72][N+:69]([O-:71])=[O:70])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:13]([O:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 311Citric AcidHCID 6375NitromethaneHCID 8857Ethyl AcetateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86758505Ethyl (E)-3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]acrylate

Product 1

HCID 18427813Ethyl 3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]-4-nitrobutanoate

Procedure

A 9.46 g (25.3 mmol) portion of ethyl (E)-3-[1-benzyloxy-3-(isoamyloxycarbonyl)cyclobutan-3-yl]acrylate was dissolved in 50 ml of nitromethane to which, while cooling in an ice bath and stirring, was subsequently added dropwise 3.78 ml (25.3 mmol) of diazabicycloundecene. After 10 minutes of stirring, the reaction mixture was further stirred at room temperature for 1 hour. While cooling in an ice bath and stirring, the reaction solution was acidified by gradually adding 10% citric acid aqueous solution and then mixed with ethyl acetate to effect separation of layers. The resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine and then dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under a reduced pressure to give 11.45 g (25.26 mmol) of the title compound. The thus obtained compound was used in the following reaction without purification.

Workup

  1. temperaturewhile cooling in an ice bath
  2. stirringAfter 10 minutes of stirring
  3. stirringthe reaction mixture was further stirred at room temperature for 1 hour
  4. temperatureWhile cooling in an ice bath
  5. stirringstirring
  6. customseparation of layers
  7. washThe resulting organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-d4d4a0f3495643bab07076476a767090
Source dataset
uspto-grants-2002_09
Patent number
US06448266B1

Reaction notes

Loading…