Dicyclohexylcarbodiimide → HCID 67800811, compound

HRID 1292610Notes

Reaction equation

HRID 1292610 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:37]1([CH2:43][C:44]2[CH:45]=[C:46]([CH:60]=[CH:61][CH:62]=2)[O:47][CH2:48]/[CH:49]=[CH:50]\[CH2:51][NH:52][C:53](=[O:59])[CH2:54][S:55][CH2:56][CH2:57][NH2:58])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>ClCCl>[N:37]1([CH2:43][C:44]2[CH:45]=[C:46]([CH:60]=[CH:61][CH:62]=2)[O:47][CH2:48]/[CH:49]=[CH:50]\[CH2:51][NH:52][C:53](=[O:59])[CH2:54][S:55][CH2:56][CH2:57][NH:58][C:9]([C:7]2[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:11])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 125775-Nitro-2-Furoic AcidHCID 757711-HydroxybenzotriazoleHCID 67649208HCID 67649208, compound

Product 1

HCID 67800811HCID 67800811, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

There was suspended 1.67 g (0.011 mol) of 5-nitro-2-furoic acid in 85 ml of dichloromethane and added 1.62 g (0.011 mol) of HOBt and 2.26 g (0.011 mol) of DCC under cooling with ice, and the mixture was stirred for 30 minutes. Thereto was added 4.0 g (0.011 mol) of N-[4-[3-(piperidinomethyl) phenoxy]-cis-2-butenyl]-2-(2-aminoethylthio)acetamide and the mixture was stirred for 18 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 ilica gel column chromatography (chloroform:methanol=10:1) to give 0.60 g of the titled compound as oily matter.

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred for 18 hours at room temperature
  3. filtrationThe precipitate was filtrated off
  4. washthe filtrate was washed with 10% aqueous solution of sodium hydroxide and with water
  5. dry with materialdried over Glauber's salt
  6. customThen the solvent was removed under reduced pressure
  7. customthe residue was purified by ilica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2f955761a1c4487c9726dc5c45704f1f
Source dataset
uspto-grants-1998_05
Patent number
US05756822

Reaction notes

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