Dicyclohexylcarbodiimide → HCID 67801386, compound

HRID 1379615Notes

Reaction equation

HRID 1379615 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][CH2:9][CH2:10][S:11][CH2:12][C:13]([OH:15])=O)=[O:7])=[CH:2]1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:41]1([CH2:47][C:48]2[CH:49]=[C:50]([CH:57]=[CH:58][CH:59]=2)[O:51][CH2:52]/[CH:53]=[CH:54]\[CH2:55][NH2:56])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>ClCCl>[N:41]1([CH2:47][C:48]2[CH:49]=[C:50]([CH:57]=[CH:58][CH:59]=2)[O:51][CH2:52]/[CH:53]=[CH:54]\[CH2:55][NH:56][C:13](=[O:15])[CH2:12][S:11][CH2:10][CH2:9][NH:8][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:7])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13104421HCID 13104421, compoundHCID 67647923HCID 67647923, compound

Product 1

HCID 67801386HCID 67801386, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was suspended 3.52 g (0.0154 mol) of 2-[(3-furoylamino)ethylthio]acetic acid in 80 ml of dichloromethane and added 2.36 g (0.0154 mol) of HOBt and 3.17 g (0.0154 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes under cooling with ice. Thereto was added 4.0 g (0.0138 mol) of 4-[3-(piperidinomethyl)phenoxy]-cis-2-butenylamine, and the mixture was stirred for 12 hours at room temperature. The precipitate was filtrated off, and the filtrate was washed with 10% 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=10:1) to give 2.9 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringthe mixture was stirred for 12 hours at room temperature
  4. filtrationThe precipitate was filtrated off
  5. washthe filtrate was washed with 10% 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=10:1)

Sources & evidence

ORD record
ord-c7d34b7f821e4936a15af03aa1482609
Source dataset
uspto-grants-1997_09
Patent number
US05672597

Reaction notes

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