Cyclopropylamine → HCID 178471863, compound

HRID 1651582Notes

Reaction equation

HRID 1651582 reaction equation
[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[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]=2)[CH2:6]1)(=[O:3])[CH3:2].[CH:30]1([NH2:33])[CH2:32][CH2:31]1>C(O)C>[C:1]([NH:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[C:15]([F:16])=[CH:14][C:13]([C:17](=[O:28])[C:18](=[CH:24][NH:33][CH:30]3[CH2:32][CH2:31]3)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:12]([F:29])[CH:11]=2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86743970HCID 86743970, compound

Product 1

HCID 178471863HCID 178471863, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20.5 g (50 mmol) of 4-[3-(acetylamino)cyclopentyl]-α-(ethoxymethylene)-2,5-difluoro-β-oxobenzenepropanoic acid, ethyl ester, in 100 ml of absolute ethanol was cooled to 10° and 3.4 g (60 mmole) of cyclopropylamine was added dropwise maintaining the temperature below 15° with an ice bath. After the addition was complete, the reaction was stirred at 5°-10° 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 and washed with ethanol and then hexane. The combined filtrate and washings were evaporated in vacuo and the residue was recrystallized from pentane to give 16.1 g of the title compound.

Workup

  1. temperaturemaintaining the temperature below 15° with an ice bath
  2. additionAfter the addition
  3. waitat room temperature for 1 hour
  4. temperatureThe resulting suspension was chilled to 5°
  5. customthe solid removed by filtration
  6. washwashed with ethanol
  7. customThe combined filtrate and washings were evaporated in vacuo
  8. customthe residue was recrystallized from pentane

Sources & evidence

ORD record
ord-654d99f1828c4970a57ba5783b3dd261
Source dataset
uspto-grants-1990_05
Patent number
US04929613

Reaction notes

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