Triethylamine → HCID 14696290, compound

HRID 1200137Notes

Reaction equation

HRID 1200137 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([NH2:26])([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl>[CH3:17][C:18]([NH:26][C:14](=[O:16])[CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 14696290HCID 14696290, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.6 g of N-benzyloxycarbonyl-β-alanine, 4.0 g of α,α-dimethylbenzylamine and 7.4 g of triethylamine were dissolved in 400 ml of anhydrous methylene chloride. To this solution were then added 8.8 g of 2-chloro-1-methylpyridinium iodide slowly at room temperature, and the mixture was heated under reflux for 2 hours. The reaction mixture was then washed, in turn, with a 10% w/v aqueous solution of sodium hydroxide, with a 1N aqueous solution of hydrochloric acid and with a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. The solution was concentrated by evaporation under reduced pressure, to give 10.7 g of crude crystals. Recrystallization of these from a mixture of hexane and benzene afforded 5.6 g (yield 56%) of the title compound melting at 96°-97° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washThe reaction mixture was then washed, in turn, with a 10% w/v aqueous solution of sodium hydroxide, with a 1N aqueous solution of hydrochloric acid and with a saturated aqueous solution of sodium chloride
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationThe solution was concentrated by evaporation under reduced pressure
  6. customto give 10.7 g of crude crystals
  7. customRecrystallization of these
  8. additionfrom a mixture of hexane and benzene

Sources & evidence

ORD record
ord-476a55f272e0443fb7891117ecc7ca04
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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