Triethylamine → 2-[beta-(2-furyl)acrylamido]-N1,N1,N5,N5-tetramethyl-pentane-1,5-diamide

HRID 64927Notes

Reaction equation

HRID 64927 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C@H:11]([C:17]([OH:19])=O)[CH2:12][CH2:13][C:14](O)=[O:15])=[O:9].C([N:22]([CH2:25]C)[CH2:23]C)C.C(Cl)(=O)OCC.Cl.[CH3:34][NH:35][CH3:36]>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][CH:11]([CH2:12][CH2:13][C:14]([N:35]([CH3:36])[CH3:34])=[O:15])[C:17]([N:22]([CH3:25])[CH3:23])=[O:19])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 10928Ethyl chloroformateHCID 54218369N-[beta-(2-furyl)acryloyl]glutamic acid

Product 1

HCID 731822862-[beta-(2-furyl)acrylamido]-N1,N1,N5,N5-tetramethyl-pentane-1,5-diamideYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of methylene chloride was suspended 5 g of the DL-N-[β-(2-furyl)acryloyl]glutamic acid, and 7 g of triethylamine was added to dissolve it. Subsequently, the resulting solution was cooled to -20° C. to -15° C., after which 4.6 g of ethyl chlorocarbonate was added dropwise, and the resulting mixture was subjected to reaction for 30 minutes. Thereafter, 3.1 g of dimethylamine hydrochloride was added, and the resulting mixture was subjected to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was washed successively with 50 ml of a 5% aqueous sodium hydroxide solution, 50 ml of diluted hydrochloric acid and 50 ml of water, and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain 3.5 g (yield 55%) of DL-2-[β-(2-furyl)acrylamido]-N1,N1,N5,N5 -tetramethyl-pentane-1,5-diamide having a melting point of 178°-180° C.

Workup

  1. additionwas added
  2. dissolutionto dissolve it
  3. temperatureSubsequently, the resulting solution was cooled to -20° C. to -15° C.
  4. customthe resulting mixture was subjected to reaction for 30 minutes
  5. customthe resulting mixture was subjected to reaction at the same temperature for 2 hours
  6. customAfter completion of the reaction
  7. washthe reaction mixture was washed successively with 50 ml of a 5% aqueous sodium hydroxide solution, 50 ml of diluted hydrochloric acid and 50 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-be6dec1f2e7545998c3db39245b54026
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Reaction notes

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