1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59347389, compound

HRID 20247Notes

Reaction equation

HRID 20247 reaction equation
C(O[CH:4]([O:17]CC)[CH2:5][CH2:6][N:7]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[C:8]([NH2:10])=[O:9])C.C1C=CC2N(O)N=NC=2C=1.[Cl:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[CH:37]=[C:36]([S:41]([CH2:44][C@@H:45]([OH:49])[C:46](O)=[O:47])(=[O:43])=[O:42])[CH:35]=[CH:34]2.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[CH:37]=[C:36]([S:41]([CH2:44][C@@H:45]([OH:49])[C:46]([N:14]1[CH2:13][CH2:12][CH:11]([N:7]3[CH2:6][CH2:5][CH:4]([OH:17])[NH:10][C:8]3=[O:9])[CH2:16][CH2:15]1)=[O:47])(=[O:42])=[O:43])[CH:35]=[CH:34]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66854329(2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acidHCID 68419696HCID 68419696, compound

Product 1

HCID 59347389HCID 59347389, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(3,3-diethoxypropyl)-N-piperidin-4-yl urea (7.79 g) obtained in Example 46a), HOBt (4.81 g) and (2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acid (9.88 g) in DMF (200 mL) was added WSC (6.02 g) at room temperature. The mixture was stirred at room temperature overnight, 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 (from ethyl acetate to ethyl acetate/ethanol=97/3) to obtain the title compound (9.41 g, 52%) 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 (from ethyl acetate to ethyl acetate/ethanol=97/3)

Sources & evidence

ORD record
ord-b2decc13343343dcad0876c97cb8c79c
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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