1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59347385, compound

HRID 2366556Notes

Reaction equation

HRID 2366556 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]2=[O:14])[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.[Cl:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([S:36]([CH2:39][C@@H:40]([OH:44])[C:41](O)=[O:42])(=[O:38])=[O:37])[CH:30]=[CH:29]2.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([S:36]([CH2:39][C@@H:40]([OH:44])[C:41]([N:1]1[CH2:2][CH2:3][CH:4]([N:7]3[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]3=[O:14])[CH2:5][CH2:6]1)=[O:42])(=[O:37])=[O:38])[CH:30]=[CH:29]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 134241411-Piperidin-4-yl-dihydropyrimidin-2,4(1H,3H)-dioneHCID 66854329(2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acid

Product 1

HCID 59347385HCID 59347385, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-piperidin-4-yl-dihydropyrimidin-2,4(1H,3H)-dione (105 mg) obtained in Example 45e), HOBt (83 mg) and (2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acid (170 mg) in DMF (10 mL) was added WSC (105 mg) at room temperature. The mixture was stirred at room temperature for 3 days, and DMF was distilled off under reduced pressure. The residue was diluted with chloroform, washed with an aqueous saturated sodium bicarbonate solution and saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1), and recrystallized from ethanol to obtain the title compound (24 mg, 9%) as a white powder.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. additionThe residue was diluted with chloroform
  3. washwashed with an aqueous saturated sodium bicarbonate solution and saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d3aa4f667075491682963f38fd2fb92b
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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