Tetrahydrofuran → 3-(4-Ethoxycarbonyloxycinnamoyl)amino-epsilon-caprolactam

HRID 1463465

Reaction equation

HRID 1463465 reaction equation
ClC([O:4][CH2:5][CH3:6])=O.O[C:8]1[CH:9]=[C:10]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[CH:11]=[CH:12][C:13]([OH:15])=O.C(N(CC)CC)C.[NH2:28][CH:29]1[CH2:36][CH2:35][CH2:34][NH:33][C:31](=[O:32])[CH2:30]1.C1C[O:40]CC1>>[CH2:5]([O:4][C:20]([O:19][C:18]1[CH:8]=[CH:9][C:10]([CH:11]=[CH:12][C:13]([NH:28][CH:29]2[CH2:36][CH2:35][CH2:34][NH:33][C:31](=[O:32])[CH2:30]2)=[O:15])=[CH:16][CH:17]=1)=[O:40])[CH3:6]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 921263-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acidHCID 215841384-Aminoazepan-2-one

Product 1

HCID 538564713-(4-Ethoxycarbonyloxycinnamoyl)amino-epsilon-caprolactam

Procedure

Ethyl chloroformate (22.2 ml) was added dropwise to a mixture of 3-hydroxy-4-methoxycinnamic acid (22.5 g), triethylamine (32.3 ml) and THF (400 ml) under ice-cooling and stirring, followed by stirring for 15 mins. Subsequently, to the mixture was added dropwise a solution of 3-amino-ε-caprolactam (14.9 g) in THF (200 ml), and then the whole was stirred for 1 hr. at room temperature. After completing the dropping, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. This solution was washed with water, dried and distilled under reduced pressure to remove the solvent. The residue was washed with ethyl acetate, dried under reduced pressure to give the title compound (28 g). This compound was used in the following reaction without purification. m.p. 209°-210°.

Workup

  1. temperaturecooling
  2. stirringby stirring for 15 mins
  3. stirringthe whole was stirred for 1 hr
  4. customat room temperature
  5. concentrationwas concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in chloroform
  7. washThis solution was washed with water
  8. customdried
  9. distillationdistilled under reduced pressure
  10. customto remove the solvent
  11. washThe residue was washed with ethyl acetate
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-7aa84c2951954b5ba91866704b3fc3c7
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Linked notes

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