1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 91488173, compound

HRID 1162350Notes

Reaction equation

HRID 1162350 reaction equation
[C:1]([NH:8][C@@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:38][N:39]1[CH2:44][CH2:43][CH:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH2:41][CH2:40]1>C(#N)C.C(N(CC)CC)C>[CH3:13][C:10]([CH3:11])([CH3:12])[C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[C:14]([N:48]1[CH2:47][CH2:46][N:45]([CH:42]2[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]2)[CH2:50][CH2:49]1)=[O:16]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid

Product 1

HCID 91488173HCID 91488173, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of Boc-D-tert-leucine (0.46 g) and HOBt (0.46 g) in acetonitrile (20 ml) was added WSC (0.58 g), and the reaction mixture was mixed at room temperature for 15 minutes. Then, 1-(1-methyl-4-piperidyl)piperazine (0.70 g) and triethylamine (0.61 g) were added, and the reaction mixture was mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (0.80 g, quantitative).

Workup

  1. additionthe reaction mixture was mixed at room temperature for 15 minutes
  2. additionthe reaction mixture was mixed at room temperature for 15 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4ee3f34ed6a44245a0804df9aa0921f8
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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