1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86759261, compound

HRID 480371Notes

Reaction equation

HRID 480371 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C[CH2:40][N:41]=[C:42]=[N:43]CCCN(C)C.Cl.NCC#N.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)[CH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](=[O:25])[N:41]([C:42]#[N:43])[CH3:40])=[CH:22][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 22502005HCID 22502005, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86759261HCID 86759261, compoundYield 500.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{[tert-Butoxycarbonyl-(4-tert-butylphenyl)amino]methyl}benzoic acid (4.1 g, 10.7mmol) was dissolved in DMF (40 ml). Hydroxybenzotriazole (1.59 g, 11.8 mmol) and EDAC (2.25 g, 1.8 mmol) were added and the reaction mixture was stirred at room temperature for 30 min. Aminoacetonitrile hydrochloride (1.38 g, 15 mmol) and diisopropylethylamine (2.55 ml, 15 mmol) were added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (150 ml) and extracted with water (125 ml). The aqueous phase was extracted with ethyl acetate (50 ml). The combined organic phases were washed with hydrochloric acid (0.2 N, 3×50 ml) and a mixture of water and saturated sodium chloride (1:1, 3×50 ml), dried (magnesium sulphate) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (150 g) using ethyl acetate/n-heptane (3:7) as eluent to afford 3.8 g of N-(4-tert-butylphenyl)-N-[4-(cyano-methylcarbamoyl)benzyl]carbamic acid tert-butyl ester.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. extractionextracted with water (125 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
  4. washThe combined organic phases were washed with hydrochloric acid (0.2 N, 3×50 ml)
  5. additiona mixture of water and saturated sodium chloride (1:1, 3×50 ml)
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (150 g)

Sources & evidence

ORD record
ord-f71c13c9589e40e791b997867806b4da
Source dataset
uspto-grants-2003_11
Patent number
US06649641B2

Reaction notes

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