Dichloromethane → HCID 58858012, compound

HRID 1162349Notes

Reaction equation

HRID 1162349 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(C)(C)C)=O.[CH:17]1[CH:18]=[CH:19][C:20]2[N:25](O)N=N[C:21]=2[CH:22]=1.CCN=C=NCCCN(C)C.[CH3:38][C:39]1[N:43]2[C:44](=[O:55])[N:45]([CH2:47][CH2:48][N: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:57]>C(N(CC)CC)C>[Cl:57][C:17]1[CH:22]=[CH:21][C:20]([NH:25][C:1]([NH:8][C@@H:9]([C:14]([N:52]2[CH2:51][CH2:50][N:49]([CH2:48][CH2:47][N:45]3[CH2:46][C:42]4=[CH:41][N:40]=[C:39]([CH3:38])[N:43]4[C:44]3=[O:55])[CH2:54][CH2:53]2)=[O:16])[C:10]([CH3:11])([CH3:12])[CH3:13])=[O:3])=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 6344Dichloromethane2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 23138420HCID 23138420, compound

Product 1

HCID 58858012HCID 58858012, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of Boc-D-tert-leucine (93 mg) in methylene chloride (2 ml) were added HOBt (81 mg), WSC (114 mg) and triethylamine (0.11 ml) under ice-cooling, and the reaction mixture was mixed at 0° C. for 30 minutes. Then, a solution of 5-methyl-2-(2-(1-piperazinyl)ethyl)-1,2-dihydroimidazo[1,5-c]imidazol-3-one (0.10 g) obtained in Example 97c) in methylene chloride (3 ml) was added, 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 potassium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/methanol=30/1) to obtain the title compound as a colorless oil (0.15 g, 79%).

Workup

  1. temperaturecooling
  2. additionthe reaction mixture was mixed at 0° C. for 30 minutes
  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 potassium 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 basic silica gel column (ethyl acetate/methanol=30/1)

Sources & evidence

ORD record
ord-e5c8acbff39e48a8812e9467f035e2f2
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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