1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 2278555, compound

HRID 1009481Notes

Reaction equation

HRID 1009481 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([N:8]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9][C:10](O)=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([N:8]([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9][C:10]([NH:31][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 754524-MethoxybenzylamineHCID 757711-HydroxybenzotriazoleHCID 4577230HCID 4577230, compound

Product 1

HCID 2278555HCID 2278555, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

707 mg of N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycine was dissolved in 8.00 mL of DMF, and 302 mg of 4-methoxybenzylamine, 324 mg of HOBt, and 460 mg of WSC were 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 saturated brine, 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=4:1) to obtain 881 mg of N2-(3-chloro-2-methylphenyl)-N-(4-methoxybenzyl)-N2-[(4-methylphenyl)sulfonyl] glycinamide.

Workup

  1. customTo the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried 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=4:1)

Sources & evidence

ORD record
ord-1b223715e7184d868b0dd57949211a0f
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

Loading…