1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 15850761, compound

HRID 1009072Notes

Reaction equation

HRID 1009072 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.[CH3:14][C:15]([O:18][C:19]([NH:21][CH2:22][CH2:23][NH2:24])=[O:20])([CH3:17])[CH3:16].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][O:12][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([NH:24][CH2:23][CH2:22][NH:21][C:19]([O:18][C:15]([CH3:17])([CH3:16])[CH3:14])=[O:20])=[O:7])[CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 15850761HCID 15850761, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Mono-methyl isophthalate (10.0 g, 55.5 mmol), t-butyl n-(2-aminoethyl)carbamate (8.89 g, 55.5 mmol, 1.0 eq) and EDCI (12.2 g, 63.8 mmol, 1.15 eq) were dissolved in 270 mL DCM, followed by the addition of DIPEA (29.0 mL, 166 mmol, 3.0 eq). The reaction was allowed to stir at room temperature overnight. It was then taken up in 100 mL of DCM, washed with a 1:1 solution of 1.0 N HCl in brine, water, and a 1:1 solution of brine in saturated NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated to afford the product as a light yellow solid (12.81 g, 72%).

Workup

  1. washwashed with a 1:1 solution of 1.0 N HCl in brine, water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64717389a5944daa83bf5b6412944c65
Source dataset
uspto-grants-2011_07
Patent number
US07973055B2

Reaction notes

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