1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69411675, compound

HRID 889846Notes

Reaction equation

HRID 889846 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12](=[O:22])[C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([OH:18])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.O.ON1[C:29]2C=CC=C[C:28]=2N=N1.C([N:36]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:37][C:38]([OH:40])=[O:39])C.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.O>[CH2:28]([O:40][C:38](=[O:39])[CH2:37][N:36]([C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[C:13]([C:12](=[O:22])[NH:11][CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)[CH:14]=1)[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH3:29]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 19755290N-Benzyl-N-ethylglycineHCID 22248625HCID 22248625, compound

Product 1

HCID 69411675HCID 69411675, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzo[1,3]dioxol-5-ylmethyl-isophthalamic acid (3.0 g, 10 mmol) in methylene chloride was added 1-hydroxy-benzotriazole monohydrate (“HOBt”) (1.35 g, 10 mmol) and ethyl N-benzylglycine (1.94 g, 10 mmol). To this was added 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (“EDAC”) (1.92 g, 10 mmol) and the mix stirred at room temperature for 24 hours. The solution treated with water (150 mL) and the organic phase separated, washed with 10% citric acid (100 mL), saturated sodium bicarbonate (100 mL) and brine (100 mL). The organic phase dried over magnesium sulfate and evaporated at reduced pressure to give ({3-[(1,3-benzodioxol-5-ylmethyl)-carbamoyl]-benzoyl}-benzyl-amino)-acetic acid ethyl ester as a solid, 3.69 g. To a solution of this ester (3.6 g, 7.6 mmol) in a mix of water (15 mL), dioxane (60 mL) and ethanol (20 mL) was added sodium hydroxide (0.72 g, 18 mmol). The mixture stirred at 50° C. for 24 hours. The solution cooled to room temperature and evaporated at reduced pressure free of solvents. The residue was diluted with water (100 mL) and washed with ether (2×50 mL). The ether discarded and the aqueous phase made acidic with 6N HCl. This was extracted with ethyl acetate (2×100 mL). The organic phases washed with brine (100 mL) and dried over magnesium sulfate. The solvent was evaporated at reduced pressure to give the title compound, 3.41 g. Microanalysis (C25H22N2O6.0.3 H2O): Calc'd: C=66.45, H=5.05, N=6.20. Found: C=66.25, H=5.15, N=5.99.

Workup

  1. customthe organic phase separated
  2. washwashed with 10% citric acid (100 mL), saturated sodium bicarbonate (100 mL) and brine (100 mL)
  3. dry with materialThe organic phase dried over magnesium sulfate
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-0bbc5fbc187949c99386d45c97da8f96
Source dataset
uspto-grants-2006_02
Patent number
US06995151B2

Reaction notes

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