1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58009604, compound

HRID 1009490Notes

Reaction equation

HRID 1009490 reaction equation
[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([N:8]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[Cl-].[NH4+].C1C=CC2N(O)N=[N:42]C=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([N:8]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH2:42])=[O:20])=[CH:21][CH:22]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 24883170HCID 24883170, compound

Product 1

HCID 58009604HCID 58009604, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

185 mg of 4-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]benzoic acid, 25 mg of ammonium chloride, and 62 mg of HOBt were dissolved in 2.00 mL of DMF, and 78 mg of WSC was added thereto, followed by stirring at room temperature overnight. To the reaction liquid was added water, followed by extraction with ethyl acetate, and the organic layer was washed with water, an aqueous sodium hydrogen carbonate solution, and water, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80 to 0:100) to obtain a product, which was recrystallized from ethanol/water (95:5) to obtain 89 mg of 4-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]benzoic acid amide.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialan aqueous sodium hydrogen carbonate solution, and water, and then dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:80 to 0:100)
  7. customto obtain a product, which
  8. customwas recrystallized from ethanol/water (95:5)

Sources & evidence

ORD record
ord-a88c0165b52f4cdebdc225baf791a038
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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