1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58859127, compound

HRID 1349460Notes

Reaction equation

HRID 1349460 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:16][O:17][CH2:18][O:19][CH3:20])[O:11][C:10]=1[C:21]([OH:23])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:40]=[CH:41][C:42]=1[Cl:43])[CH2:28][NH:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:16][O:17][CH2:18][O:19][CH3:20])[O:11][C:10]=1[C:21]([N:29]([CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:28][C:27]1[CH:40]=[CH:41][C:42]([Cl:43])=[C:25]([Cl:24])[CH:26]=1)=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 23077631HCID 23077631, compoundHCID 58859150HCID 58859150, compound

Product 1

HCID 58859127HCID 58859127, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxy-6-methoxymethoxymethyl-4-oxo-4H-pyran-2-carboxylic acid (658 mg) obtained in Step 4 was dissolved in dimethylformamide (5 ml), and tert-butyl [2-(3,4-dichlorobenzylamino)ethyl]carbamate (596 mg) obtained in Step 1, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (429 mg) and 1-hydroxybenzotriazole (343 mg) were added at room temperature, and the mixture was stirred for 1 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the obtained reaction mixture and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=15:1) to give crude tert-butyl {2-[N-(3-benzyloxy-6-methoxymethoxymethyl-4-oxo-4H-pyran-2-carbonyl)-N-(3,4-dichlorobenzyl)amino]ethyl}carbamate (1.12 g).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-91329ae795b74a8d965b3b5b79600621
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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