1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1''-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}-1,4''-bipiperidin-2-one

HRID 20214Notes

Reaction equation

HRID 20214 reaction equation
CCN=C=NCCCN(C)C.[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23]([CH2:26][C@@H:27]([OH:31])[C:28]([OH:30])=O)(=[O:25])=[O:24])[CH:17]=[CH:16]2.[N:32]1([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([S:23]([CH2:26][C@@H:27]([OH:31])[C:28]([N:42]1[CH2:41][CH2:40][CH:39]([N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][C:33]3=[O:38])[CH2:44][CH2:43]1)=[O:30])(=[O:24])=[O:25])[CH:17]=[CH:16]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21839852[1,4'-Bipiperidin]-2-oneHCID 66854329(2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acid

Product 1

HCID 115838001''-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropanoyl}-1,4''-bipiperidin-2-oneYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC (0.19 g) was added to a mixture of (2S)-3-[(6-chloronaphthalen-2-yl)sulfonyl]-2-hydroxypropionic acid (0.31 g), 1,4′-bipiperidin-2-one (0.18 g) and HOBt (0.15 g) in DMF (15 mL) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and diluted with dichloromethane and an aqueous sodium bicarbonate solution. The organic layer was separated, 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) to obtain the title compound (0.26 g, 54%) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with dichloromethane
  3. customThe organic layer was separated
  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)

Sources & evidence

ORD record
ord-c5f16dba08814d3e8444b69460007b9d
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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