Dicyclohexylcarbodiimide → HCID 22906824, compound

HRID 1379608Notes

Reaction equation

HRID 1379608 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][CH2:9][CH2:10][S:11]([CH2:13][C:14]([OH:16])=O)=[O:12])=[O:7].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:42]1([CH2:48][C:49]2[CH:50]=[C:51]([CH:57]=[CH:58][CH:59]=2)[O:52][CH2:53][CH2:54][CH2:55][NH2:56])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl>[N:42]1([CH2:48][C:49]2[CH:50]=[C:51]([CH:57]=[CH:58][CH:59]=2)[O:52][CH2:53][CH2:54][CH2:55][NH:56][C:14](=[O:16])[CH2:13][S:11]([CH2:10][CH2:9][NH:8][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])=[O:12])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 18915877HCID 18915877, compound

Product 1

HCID 22906824HCID 22906824, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was suspended 3.0 g (0.0122 mol) of 2-[2-(2-furoylamino)ethylsulfinyl]acetic acid in 100 ml of dichloromethane and added 1.87 g (0.0122 mol) of HOBt and 2.52 g (0.0122 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 3.04 g (0.0122 mol) of N-3-[3-(piperidinomethyl)phenoxy]propylamine, and the mixture was stirred for 18 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with 5% aqueous solution of sodium hydroxide and with water and dried over Glauber's salt. Then the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=5:1) to give 3.0 g of the titled compound as crystals.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 18 hours at room temperature
  4. filtrationThe precipitate was filtrated off
  5. washthe filtrate was washed with 5% aqueous solution of sodium hydroxide and with water
  6. dry with materialdried over Glauber's salt
  7. customThen the solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-9944e21591bf4e689cc46e17c41f25d8
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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