Triethylamine → HCID 10298335, compound

HRID 2222456Notes

Reaction equation

HRID 2222456 reaction equation
[Cl-].[NH3+:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:7][C:8]1([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11][CH2:10][O:9]1.[Cl:22][C:23]1[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH3:35])[CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C)C=O.C(OCC)(=O)C.O>[Cl:22][C:23]1[CH:31]=[C:30]([O:32][CH2:33][CH2:34][CH3:35])[CH:29]=[CH:28][C:24]=1[C:25]([NH:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH2:7][C:8]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][O:9]1)=[O:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 224943262-Chloro-4-propoxybenzoic acidHCID 86596097HCID 86596097, compound

Product 1

HCID 10298335HCID 10298335, compoundYield 60.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.091 g of methyl 2-[3-(ammoniomethyl)-4-methoxybenzyl]tetrahydro-2-furancarboxylate chloride and 0.074 g of 2-chloro-4-propoxybenzoic acid in 2.5 ml of N,N-dimethylformamide were added 0.119 μl of triethylamine and 0.119 μl of diethyl cyanophosphonate, and the mixture was stirred at room temperature for 4 hours. 10 ml of water and 10 ml of ethyl acetate were added, and the organic layer was evaporated. The residue was dissolved in 2.5 ml of ethanol, 0.3 ml of 5N sodium hydroxide was added, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated, and 5 ml of ethyl acetate, 2.5 ml of water and 0.5 ml of 5N hydrochloric acid were added. The organic layer was concentrated, and the residue was purified by HPLC, to give 0.081 g of the title compound as a white solid.

Workup

  1. customthe organic layer was evaporated
  2. dissolutionThe residue was dissolved in 2.5 ml of ethanol
  3. addition0.3 ml of 5N sodium hydroxide was added
  4. stirringthe mixture was stirred at room temperature for 14 hours
  5. concentrationThe reaction mixture was concentrated
  6. addition5 ml of ethyl acetate, 2.5 ml of water and 0.5 ml of 5N hydrochloric acid were added
  7. concentrationThe organic layer was concentrated
  8. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-1524615ae3ce4aaf87289c00fa09a554
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

Loading…