Diisopropylcarbodiimide → HCID 68817196, compound

HRID 732500Notes

Reaction equation

HRID 732500 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-methylpyrrolidine (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-9eea8679d50d444498e80cdce818de76
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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