1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21939821, compound

HRID 1242946Notes

Reaction equation

HRID 1242946 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH2:28]([O:35][C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][C:46](O)=[O:47])=[CH:41][CH:40]=1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(OCC)(=O)C.O.O1CCCC1.C(N(CC)CC)C>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:46](=[O:47])[CH2:45][C:42]1[CH:41]=[CH:40][C:39]([NH:38][C:36](=[O:37])[O:35][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:44][CH:43]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 21939874HCID 21939874, compound

Product 1

HCID 21939821HCID 21939821, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethylethylenediamine (0.64 ml), WSC (1.31 g), HOBt (1.05 g), and triethylamine (2.4 ml) were added to a tetrahydrofuran (50 ml) solution of 2-[4-[[(benzyloxy)carbonyl]amino]phenyl]acetic acid (1.5 g) obtained in Reference Example 90. After stirring for 20 hours, the reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried and then concentrated. The residue was recrystallized from ethyl acetate-hexane, to give the titled compound (1.72 g).

Workup

  1. customobtained in Reference Example 90
  2. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8dfda3bbdcf642c293652d5e9122c151
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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