Triethylamine → HCID 131716925, compound

HRID 1086283Notes

Reaction equation

HRID 1086283 reaction equation
Cl.[NH:2]1[CH2:13][S:12][CH2:11][C@H:3]1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH:22]1[CH2:30][CH2:31][C:32](O)=[O:33].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH:22]1[CH2:30][CH2:31][C:32]([CH:11]1[S:12][CH2:13][NH:2][C@@H:3]1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103976563-(indan-2-yl)propionic acidHCID 1317169261-L-thioprolylpyrrolidine hydrochloride

Product 1

HCID 131716925HCID 131716925, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.89 g of 1-L-thioprolylpyrrolidine hydrochloride was suspended in 20 ml of methylene chloride. To the suspension were added 0.40 g of triethylamine and 0.76 g of 3-(indan-2-yl)propionic acid under ice-cooling with stirring. After 10 minutes, 0.92 g of WSC.HCl was added to the mixture under ice-cooling while stirring. The mixture was sirred for 16 hours at room temperature. The reaction mixture was washed with diluted hydrochloric acid, water, and saturated sodium hydrogen carbonate in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was recrystallized from ethyl acetate/isopropyl ether to produce 1.02 g of 1-{3-[3-(indan-2-yl)proprionyl]-L-thioprolyl]pyrrolidine as colorless crystals (yield: 71%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringwhile stirring
  4. waitThe mixture was sirred for 16 hours at room temperature
  5. washThe reaction mixture was washed with diluted hydrochloric acid, water, and saturated sodium hydrogen carbonate in this order
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue thus obtained
  9. customwas recrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-8934757dee024834a65364921630c9dc
Source dataset
uspto-grants-1991_07
Patent number
US05028604

Reaction notes

Loading…