Dicyclohexylcarbodiimide → HCID 9956144, compound

HRID 1379621Notes

Reaction equation

HRID 1379621 reaction equation
[CH2:1]([O:3][C:4]([NH:6][CH2:7][CH2:8][S:9]([CH2:11][C:12]([OH:14])=O)=[O:10])=[O:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:40]1([CH2:46][C:47]2[CH:48]=[C:49]([CH:56]=[CH:57][CH:58]=2)[O:50][CH2:51]/[CH:52]=[CH:53]\[CH2:54][NH2:55])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1>CN(C)C=O.ClCCl>[N:40]1([CH2:46][C:47]2[CH:48]=[C:49]([CH:56]=[CH:57][CH:58]=2)[O:50][CH2:51]/[CH:52]=[CH:53]\[CH2:54][NH:55][C:12](=[O:14])[CH2:11][S:9]([CH2:8][CH2:7][NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:10])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13104421HCID 13104421, compoundHCID 18915902HCID 18915902, compound

Product 1

HCID 9956144HCID 9956144, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

There was dissolved 1.64 g (0.0074 mol) of 2-[2-(ethoxycarbonylamino)ethylsulfinyl]acetic acid in 80 ml of 50% dimethylformamide-dichloromethane and added 1.13 g (0.0074 mol) of HOBt and 1.52 g (0.0074 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 1.91 g (0.0074 mol) of 4-[3-(piperidinomethyl)-phenoxy]-cis-2-butenylamine and the mixture was stirred for 18 hours at room temperature. The obtained precipitate was filtrated off, and the filtrate was washed with 5% aqueous solution of sodium hydroxide and with water successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1). Then the obtained crystals were recrystallized from ethyl acetate-n-hexane (1:1) to give 1.3 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 18 hours at room temperature
  4. filtrationThe obtained precipitate was filtrated off
  5. washthe filtrate was washed with 5% aqueous solution of sodium hydroxide and with water successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)
  9. customThen the obtained crystals were recrystallized from ethyl acetate-n-hexane (1:1)

Sources & evidence

ORD record
ord-fed0cd8579df40a2bbaa35ada555f4d9
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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