1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 91465240, compound

HRID 1162345Notes

Reaction equation

HRID 1162345 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][C:39]1[N:43]2[C:44](=[O:55])[N:45]([CH2:47][CH2:48][CH:49]3[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]3)[CH2:46][C:42]2=[CH:41][N:40]=1>C(Cl)Cl.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:52]1[CH2:53][CH2:54][CH:49]([CH2:48][CH2:47][N:45]2[CH2:46][C:42]3=[CH:41][N:40]=[C:39]([CH3:38])[N:43]3[C:44]2=[O:55])[CH2:50][CH2:51]1)=[O:16]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 23138322HCID 23138322, compound

Product 1

HCID 91465240HCID 91465240, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of Boc-D-tert-leucine (0.69 g) in methylene chloride (15 ml) were added HOBt (0.61 g), WSC (0.86 g) and triethylamine (0.84 ml) under ice-cooling. The reaction mixture was mixed at 0° C. for 2.5 hours. Then, 5-methyl-2-(2-(4-piperidinyl)ethyl)-1,2-dihydroimidazo[1,5-c]imidazol-3-one (0.74 g) obtained in Example 96b) was added thereto, and further 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 magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with silica gel column (ethyl acetate/methanol=20/1) to obtain the title compound as colorless powder (0.95 g, 69%).

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was mixed at 0° C. for 2.5 hours
  3. additionfurther mixed at room temperature for 15 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified with silica gel column (ethyl acetate/methanol=20/1)

Sources & evidence

ORD record
ord-8a557304ed9d4c778f3df96bf41998d8
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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