1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67241283, compound

HRID 1949476Notes

Reaction equation

HRID 1949476 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][O:17][C:18](=[O:22])[CH2:19][CH2:20][NH2:21].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>ClCCl.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12](=[O:14])[NH:21][CH2:20][CH2:19][C:18]([O:17][CH3:16])=[O:22])[CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 67241283HCID 67241283, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (0.4 g, 1.98 mmol) and 3-amino-propionic acid methyl ester hydrochloride (0.277 g, 1.98 mmol) in dichloromethane (16 mL) and THF (6 mL) was treated with diisopropylethylamine (0.256 g, 1.98 mmol); it was then added EDCI (0.42 g, 2.18 mmol) and dimethylaminopyridine (0.073 g, 0.59 mmol). The reaction mixture was stirred at room temperature for 50 hours and rotavapored to dryness. The residue was dissolved in dichloromethane. The dichloromethane layer was then successively washed with aqueous 5% citric acid, aqueous saturated hydrogenocarbonate solution, brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield the title compound as a gum (551 mg, 97%).

Workup

  1. washThe dichloromethane layer was then successively washed with aqueous 5% citric acid, aqueous saturated hydrogenocarbonate solution, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-fce5dcc7a30646878259026ef6b43288
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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