Dicyclohexylcarbodiimide → HCID 178473054, compound

HRID 1683303Notes

Reaction equation

HRID 1683303 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([C:15]([O-:17])=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][N:52]=[C:53]([NH:62][C:63](=[O:69])[O:64][C:65]([CH3:68])([CH3:67])[CH3:66])[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58]>ClCCl>[CH3:67][C:65]([CH3:68])([O:64][C:63]([NH:62][C:53]([NH:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][NH:43][C:15](=[O:17])[CH:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:54][C:55]([O:56][C:57]([CH3:58])([CH3:59])[CH3:60])=[O:61])=[O:69])[CH3:66]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 25214054Bis(1,1-dimethylethyl) [[(8-aminooctyl)imino]methylene]biscarbamateHCID 86750947Ethyl 2-phenylmethoxypropanedioate

Product 1

HCID 178473054HCID 178473054, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2.6 g (10.9.10-3 mol) of ethyl 2-phenylmethoxypropanedioate are dissolved in 50 ml of dichloromethane and the mixture is cooled to 0° C. 4.34 g (22.10-3 mol) of N,N'-dicyclohexylcarbodiimide and 0.57 g (4.10-3 mol) of 1-hydroxybenzotriazole are added, the mixture is stirred for 0.5 hour, a solution of 4.21 g (10.9. 10-3 mol) of bis(1,1-dimethylethyl) [[(8-aminooctyl)imino]methylene]biscarbamate in 15 ml of dichloromethane is then added and the mixture is stirred at room temperature for 48 hours. The reaction medium is concentrated under reduced pressure and the residue is then purified by chromatography on silica using a methylcyclohexane/ethyl acetate mixture (7/3) as the eluent to give 2.7 g (yield=40.8%) of the expected product in the form of a pale yellow oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 48 hours
  2. concentrationThe reaction medium is concentrated under reduced pressure
  3. customthe residue is then purified by chromatography on silica using a methylcyclohexane/ethyl acetate mixture (7/3) as the eluent

Sources & evidence

ORD record
ord-2ef0cf1e539e45c69803c5fb9e2aecdb
Source dataset
uspto-grants-1997_06
Patent number
US05637613

Reaction notes

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