Dicyclohexylcarbodiimide → HCID 178472241, compound

HRID 1683302Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.C1(N=C=NC2CCCCC2)CCCCC1.O.ON1C2C=CC=CC=2N=N1.[NH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:43]=[C:44]([NH:53][C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])[NH:45][C:46](=[O:52])[O:47][C:48]([CH3:51])([CH3:50])[CH3:49]>C(Cl)(Cl)Cl>[CH3:58][C:56]([CH3:59])([O:55][C:54]([NH:53][C:44]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][NH:36][C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[N:45][C:46]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:52])=[O:60])[CH3:57]

Participants

Conditions

Temperature: 0 °C

Procedure

1.05 g (8.10-3 mol) of monoethyl malonate are dissolved in 15 ml of anhydrous chloroform, the solution is then cooled to 0° C. and 1.65 g (8.10-3 mol) of 1,3-dicyclohexylcarbodiimide and 0.108 g (0.8.10-3 mol) of 1-hydroxybenzotriazole hydrate are added. After stirring for 0.5 hour at 0° C., a solution of 1.5 g (4.19.10-3 mol) of bis(1,1-dimethylethyl) [[(6-aminohexyl)imino]methylene]biscarbamate in 5 ml of anhydrous chloroform is added. The mixture is then stirred for 48 hours at room temperature, after which the reaction medium is concentrated under reduced pressure. The crude product obtained is purified by medium pressure chromatography on silica using a hexane/ethyl acetate mixture (1/1 v/v) as the eluent to give 1.95 g (yield=99%) of the expected product in the form of a yellow oil.

Workup

stirringThe mixture is then stirred for 48 hours at room temperature
concentrationafter which the reaction medium is concentrated under reduced pressure
customThe crude product obtained
customis purified by medium pressure chromatography on silica using a hexane/ethyl acetate mixture (1/1 v/v) as the eluent

Sources & evidence

ORD record: ord-f01456e44df54e33b4a3d2f5c48fc4df
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637613

Reaction notes

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