Triethylamine → HCID 68556252, compound

HRID 539389Notes

Reaction equation

HRID 539389 reaction equation
[C:1]12([C:8]([OH:10])=[O:9])CC(C[CH2:6]1)C=[CH:2]2.Cl.[CH3:12]N(C)CCCN=C=NCC.O.ON1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH:28]12[CH2:12][CH:31]([CH:32]=[CH:33]1)[CH2:30][CH:29]2[C:8]([OH:10])=[O:9].[CH3:6][C:1](=[CH:2][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]([OH:10])=[O:9]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1785159515023-39-9

Product 1

HCID 68556252HCID 68556252, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

11 g (79.64 mmol) of norbornene carboxylic acid (produced from Aldrich Inc.), 12.9 g (72.4 mmol) of 4-hydroxy methylcinnamate prepared according to Example 4, 22.2 g (115.84 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (produced from Aldrich Inc.), and 14.7 g (108.6 mmol) of 1-hydroxybenzotriazole hydrate (HOBT) (produced from Aldrich Inc.) were dissolved in 100 ml of DMF in a 250 ml 2-neck flask. The temperature of the resulting solution was decreased to 0° C. and then 50 ml (362 mmol) of triethylamine was slowly dropped thereto. The temperature of the resulting solution was increased to room temperature and then the a reaction was performed for 3 hours. After the reaction was completed, the result was extracted using an excess amount of ethyl acetate. The extract was washed using NaHCO3 and H2O, dried over anhydrous MgSO4, and then filtered. The solvent of the filtrate was removed using a rotary evaporator to produce a yellow solid product, which was refined using a column chromatography (Hexane:Ethyl acetate=6:1) to attain a pure product. (Yield: 60%)

Workup

  1. customwas decreased to 0° C.
  2. extractionthe result was extracted
  3. washThe extract was washed
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe solvent of the filtrate was removed
  7. customa rotary evaporator
  8. customto produce a yellow solid product, which

Sources & evidence

ORD record
ord-fafd41a207154634b38c2fb4ec951cf3
Source dataset
uspto-grants-2014_10
Patent number
USRE045219E1

Reaction notes

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