Triethylamine → HCID 53927192, compound

HRID 2073226Notes

Reaction equation

HRID 2073226 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].C(N(CC)CC)C.[CH3:15][O:16][C:17](=[O:33])[C@H:18]([CH3:32])[NH:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]([CH3:30])[C:21]=1[CH3:31]>C1(C)C=CC=CC=1>[CH3:15][O:16][C:17](=[O:33])[C@H:18]([CH3:32])[N:19]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]([CH3:30])[C:21]=1[CH3:31])[C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chlorideHCID 53663888HCID 53663888, compound

Product 1

HCID 53927192HCID 53927192, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

During 30 minutes 0.07 g-moles of ethoxyacetyl chloride, dissolved in 20 ml of toluene, and 0.07 g-moles of triethylamine, dissolved in 20 ml of toluene, are dropped at room temperature simultaneously to 0.06 g-moles of N-(2,3-dimethylnaphthyl)-alanine methyl ester, dissolved in 100 ml of toluene. Thereby the temperature rises to 43°. The reaction mixture is then stirred at about 40° during 12 hours. From the resulting yellow suspension the inorganic salt is filtered off and the filtrate is washed with water until neutral. Then the organic phase is dried over sodium sulfate and concentrated by evaporation. The crude oil is purified by column chromatography using silicagel 60 and diethylether as the eluant. After removal of the solvent 18.8 g (=91% of theory) of the final product are obtained in crystallised form, m.p. 96° to 108°.

Workup

  1. customrises to 43°
  2. filtrationFrom the resulting yellow suspension the inorganic salt is filtered off
  3. washthe filtrate is washed with water until neutral
  4. dry with materialThen the organic phase is dried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe crude oil is purified by column chromatography
  7. customAfter removal of the solvent 18.8 g (=91% of theory) of the final product
  8. customare obtained in crystallised form, m.p. 96° to 108°

Sources & evidence

ORD record
ord-1325f41de3f4488288b755c18b5c6f45
Source dataset
uspto-grants-1990_04
Patent number
US04916157

Reaction notes

Loading…