Diethylamine → HCID 14217110, compound

HRID 1855696Notes

Reaction equation

HRID 1855696 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]([NH:14][C:15](=[O:17])[CH3:16])=[C:5](OS(C)(=O)=O)[CH2:6][O:7][CH3:8].C(NCC)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:18])/[C:4](/[NH:14][C:15](=[O:17])[CH3:16])=[CH:5]/[CH2:6][O:7][CH3:8]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54080242HCID 54080242, compound

Product 1

HCID 14217110HCID 14217110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution consisting of 27.6 g (0.098 mol) of mesylate 9, 20.5 ml of diethylamine and 250 ml of methylene chloride was heated at reflux temperature for 2 hrs under an atmosphere of argon. The resultant solution was cooled, concentrated in vacuo and the residue filtered through a column of silica gel (125 g) using ethyl acetate as the eluent. The fractions containing product (as determined by thin layer chromatography) were combined and concentrated in vacuo. Crystallization of the residue from ether/petroleum ether (bp 35°-60°) yielded Z-2-acetamido-4-methoxy-2-butenoic acid methyl ester (4) identical to the material obtained by the previous method (Examples 1 and 2). The mother liquors from the crystallization of 4 were concentrated in vacuo to yield an oil which contained a 1:1 mixture of 4 and E-2-acetamido-4-methoxy-2-butenoic acid methyl ester (5).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 hrs under an atmosphere of argon
  3. concentrationconcentrated in vacuo
  4. filtrationthe residue filtered through a column of silica gel (125 g)
  5. additionThe fractions containing product (as determined by thin layer chromatography)
  6. concentrationconcentrated in vacuo
  7. customCrystallization of the residue from ether/petroleum ether (bp 35°-60°)

Sources & evidence

ORD record
ord-55138c05216448ee8b115a116f9c6c78
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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