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

HRID 20245Notes

Reaction equation

HRID 20245 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 4 5e), 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-316c0fc531f442d18355a8b989d9b6e6
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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