Triethylamine → HCID 19790977, compound

HRID 1655756Notes

Reaction equation

HRID 1655756 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].C(N(CC)CC)C.[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH:8][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:22]([O:21][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:23])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 5458485-(((Tert-butoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 19790977HCID 19790977, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 7.68 g of β-alanine ethyl ester hydrochloride in 50 ml of methylene chloride there was added, with stirring, 5.56 g of triethyl- amine. 10.86 g of N-t-butoxycarbonyl-5-aminovaleric acid, dissolved in 50 ml of methylene chloride, and portionwise 11.35 g of DCC, in that order. After completion of the addition, the reaction mixture was stirred at room temperature overnight and filtered off from separated urea. The filtrate was washed in succession with 250 ml of sodium bicarbonate solution (5%), water, 250 ml of 0.1M citric acid and, finally, with saturated sodium chloride solution. Thereafter, the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography on silica gel, to obtain N-[5-(1-t-butoxyformamido)valeryl]-β-alanine ethyl ester in 59% yield, melting point 28° (from hexane).

Workup

  1. additionthere was added
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. filtrationfiltered off
  5. customfrom separated urea
  6. washThe filtrate was washed in succession with 250 ml of sodium bicarbonate solution (5%), water, 250 ml of 0.1M citric acid
  7. customThereafter, the solvent was evaporated under reduced pressure
  8. customthe oily residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-34c0bad0fd3a4c6b952227ab7cb33e1f
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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