Triethylamine → 2-[beta-(2-furyl)acrylamido]-N1,N5-bis(3-methyl-2-butenyl)pentane-1,5-diamide

HRID 64930Notes

Reaction equation

HRID 64930 reaction equation
O[N:2]1[C:6](=O)[CH2:5][CH2:4][C:3]1=O.Cl.[CH3:10][C:11]([CH3:15])=[CH:12][CH2:13][NH2:14].[CH2:16](N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1.[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH:43]=[CH:44][C:45]([NH:47][C@H:48]([C:54]([OH:56])=O)[CH2:49][CH2:50][C:51]([OH:53])=O)=[O:46]>C(Cl)Cl>[O:38]1[CH:42]=[CH:41][CH:40]=[C:39]1[CH:43]=[CH:44][C:45]([NH:47][CH:48]([CH2:49][CH2:50][C:51]([NH:2][CH2:6][CH:5]=[C:4]([CH3:16])[CH3:3])=[O:53])[C:54]([NH:14][CH2:13][CH:12]=[C:11]([CH3:15])[CH3:10])=[O:56])=[O:46]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 183265643-Methylbut-2-en-1-amine hydrochlorideHCID 54218369N-[beta-(2-furyl)acryloyl]glutamic acid

Product 1

HCID 30633562-[beta-(2-furyl)acrylamido]-N1,N5-bis(3-methyl-2-butenyl)pentane-1,5-diamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 300 ml of methylene chloride was dissolved 5 g of the DL-N-[β-(2-furyl)acryloyl]glutamic acid, and thereto were successively added 5.4 g of N-hydroxysuccinimide, 5 g of (3-methyl-2-butenyl)amine hydrochloride, 5 g of triethylamine and 9.6 g of dicyclohexylcarbodiimide at room temperature, and the resulting mixture was stirred for 6 hours. Subsequently, the precipitated dicyclohexylurea was removed by filtration, and the filtrate thus obtained was washed successively with 100 ml of diluted hydrochloric acid, 100 ml of a 5% aqueous sodium hydroxide solution and 100 ml of water, and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure to obtain 4 g (yield 51%) of DL-2-[β-(2-furyl)acrylamido]-N1,N5 -bis(3-methyl-2-butenyl)pentane-1,5-diamide having a melting point of 199°-203° C.

Workup

  1. customat room temperature
  2. customSubsequently, the precipitated dicyclohexylurea was removed by filtration
  3. customthe filtrate thus obtained
  4. washwas washed successively with 100 ml of diluted hydrochloric acid, 100 ml of a 5% aqueous sodium hydroxide solution and 100 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-b844956002ed49109d8001d09fed1453
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Reaction notes

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