Diisopropylcarbodiimide → HCID 68817196, compound

HRID 1436643Notes

Reaction equation

HRID 1436643 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.[CH2:7]([O:9][C:10](=[O:27])[C:11]1[CH:19]=[C:18]([C:20](=[O:26])[N:21]([CH3:25])[CH2:22][CH2:23][CH3:24])[CH:17]=[C:13]([C:14](O)=[O:15])[CH:12]=1)[CH3:8].ON1C2C=CC=CC=2N=N1.C(N=C=NC(C)C)(C)C>ClCCl>[CH2:7]([O:9][C:10](=[O:27])[C:11]1[CH:12]=[C:13]([C:14]([N:3]2[CH2:4][CH2:5][CH2:6][CH:2]2[CH3:1])=[O:15])[CH:17]=[C:18]([C:20]([N:21]([CH3:25])[CH2:22][CH2:23][CH3:24])=[O:26])[CH:19]=1)[CH3:8]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 130032-MethylpyrrolidineHCID 757711-HydroxybenzotriazoleHCID 688146805-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl ester

Product 1

HCID 68817196HCID 68817196, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 2-methyl pyrrolidine (204 mg, 2.4 mmol) to a solution of 5-(methyl-propylcarbamoyl)-isophthalic acid monoethyl ester (640 mg, 2.18 mmol) in dichloromethane (8 mL) followed by 1-hydroxybenzotriazole (20 mg, 0.15 mmol) and diisopropyl carbodiimide (375 μL, 2.4 mmol). Stir the solution at room temperature over the weekend. Add ethyl acetate (25 mL) and wash with saturated aqueous ammonium chloride (2×10 mL), saturated aqueous sodium bicarbonate (10 mL), saturated aqueous sodium chloride (10 mL), dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound as an oil (218 mg, 28%).

Workup

  1. washAdd ethyl acetate (25 mL) and wash with saturated aqueous ammonium chloride (2×10 mL), saturated aqueous sodium bicarbonate (10 mL), saturated aqueous sodium chloride (10 mL)
  2. dry with materialdry (sodium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f0df7423eb804ac69d461f4b123f9a3f
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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