Triethylamine → HCID 13040912, compound

HRID 544422Notes

Reaction equation

HRID 544422 reaction equation
[O:1]1[CH2:17][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1.[ClH:18].[NH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>C(O)(C)C>[ClH:18].[OH:1][CH:2]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=1)[CH2:17][NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 13040891Methyl 3-{4-[(oxiran-2-yl)methoxy]phenyl}propanoate

Product 1

HCID 13040912HCID 13040912, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5 gm (0.02 mole of methyl 3-[4-(2,3-epoxypropoxy)phenyl]propionate, 3 gm (0.02 mole) of ethyl 3-aminopropionate hydrochloride and 2.8 ml (0.02 mole) of triethylamine in25 mL of isopropanol was heated to reflux for 4 hours. The reaction medium was then cooled and the triethylamine hydrochloride side-product which crystallized was removed by filtration. The mother liquor was then evaporated under reduced pressure and the resulting residue taken up in ethanol and treated with ethereal HCl to provide 1 gm (12%) as a crystalline solid: mp 110°-111°. The NMR spectrum was consistent with the assigned structure and the elemental analysis was consistent with the formula C18H28NO6Cl.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction medium was then cooled
  4. customthe triethylamine hydrochloride side-product which crystallized
  5. customwas removed by filtration
  6. customThe mother liquor was then evaporated under reduced pressure
  7. additiontreated with ethereal HCl
  8. customto provide 1 gm (12%) as a crystalline solid

Sources & evidence

ORD record
ord-2ff382df69e24c36a53f8f8f3a7e467b
Source dataset
uspto-grants-1984_05
Patent number
US04450173

Reaction notes

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