Cyclopropylamine → HCID 178471862, compound

HRID 1651587Notes

Reaction equation

HRID 1651587 reaction equation
[O:1]1[C:5]2([CH2:9][CH2:8][CH:7]([C:10]3[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:28])[C:18](=[CH:24]OCC)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([F:29])[CH:11]=3)[CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>C(O)C>[CH:30]1([NH:33][CH:24]=[C:18]([C:17](=[O:28])[C:13]2[CH:14]=[C:15]([F:16])[C:10]([CH:7]3[CH2:8][CH2:9][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6]3)=[CH:11][C:12]=2[F:29])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86743972HCID 86743972, compound

Product 1

HCID 178471862HCID 178471862, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20.5 g (50 mmol) of 4-(1,4-dioxaspiro[4.4]non-7-yl)-α-(ethoxymethylene)-2,5-difluoro-β-oxobenzenepropanoic acid, ethyl ester in 200 ml of ethanol was cooled to 10° and treated dropwise with 3.4 g (60 mmol) of cyclopropylamine maintaining the temperature below 15° with an ice bath. After the addition was complete, the reaction was stirred at 5°-15° for 1.5 hours and then at room temperature for 1 hour. The resulting suspension was chilled to 5° and the solid removed by filtration, washed with ethanol, then hexane. The combined filtrate and washings were evaporated in vacuo and the residue was recrystallized from hexane to give 17.5 g of the title compound.

Workup

  1. additionAfter the addition
  2. waitat room temperature for 1 hour
  3. temperatureThe resulting suspension was chilled to 5°
  4. customthe solid removed by filtration
  5. washwashed with ethanol
  6. customThe combined filtrate and washings were evaporated in vacuo
  7. customthe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-0705ece6f5c04588a8319119aa27ee71
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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