Dicyclohexylcarbodiimide → HCID 22101917, compound

HRID 1458298Notes

Reaction equation

HRID 1458298 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:47][CH:48]1[CH2:52][N:51]([CH2:53][CH3:54])[N:50]([CH2:55][CH3:56])[CH2:49]1>>[CH2:55]([N:50]1[CH2:49][CH:48]([NH:47][C:19](=[O:21])[CH2:18][C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:1]/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4])=[CH:17][CH:16]=2)[CH2:52][N:51]1[CH2:53][CH3:54])[CH3:56]

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5591991,2-Diethyl-4-pyrazolidinamineHCID 69306561HCID 69306561, compound

Product 1

HCID 22101917HCID 22101917, compoundYield 95.3%

Procedure

To a solution of 4-geranyloxyphenylacetic acid (1.50 g) in tetrahydrofuran anhydride (30 ml) were added 1- hydroxybenzotriazole (0.85 g), N,N'- dicyclohexyl carbodiimide (1.29 g), and 4-amino-1,2- diethylpyrazolidine (0.75 g) while being cooled with ice and then the mixture was stirred for 6 hours at room temperature. The reaction solution was filtered so as to filter out the deposited product and the filtrate was concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1), thereby yielding 2.05 g (95%) of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. filtrationThe reaction solution was filtered so as
  3. filtrationto filter out the deposited product
  4. concentrationthe filtrate was concentrated under a vacuum
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-3a89a3ac7e3d44fa9995d4be4d70984c
Source dataset
uspto-grants-1998_12
Patent number
US05849930

Reaction notes

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