Dicyclohexylcarbodiimide → HCID 86637944, compound

HRID 1675389Notes

Reaction equation

HRID 1675389 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5](/[CH:10]=[CH:11]/[C:12]([CH2:14][C:15](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:24]([O:25][CH3:26])[C:22]([OH:23])=[CH:21][CH:20]=2)=[O:16])=[O:13])[CH:4]=1.[OH:28]N1C2C=CC=CC=2N=N1.[CH:38]([NH:40][CH:41]([CH2:45][CH3:46])[C:42]([OH:44])=[O:43])=[O:39].C1(N=C=[N:55][CH:56]2CCCCC2)CCCCC1>N1C=CC=CC=1.ClCCl>[CH3:26][O:25][C:24]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19](/[CH:18]=[CH:17]/[C:15]([CH2:14][C:12](/[CH:11]=[CH:10]/[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=2)=[O:13])=[O:16])[CH:27]=1.[CH:38]([NH:40][C:41]([NH:55][CH:56]=[O:28])([CH2:45][CH3:46])[C:42]([O-:44])=[O:43])=[O:39]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5594552-N-FORMYLAMIONO-BUTYRICACIDHCID 969516Curcumin

Product 1

HCID 86637944HCID 86637944, compoundYield 313.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a slurry of 1.85 g curcumin (5 mmole), 0.14 g 1-hydroxybenzotriazole (1 mmole) and 1.6 g N-formylaminobutyric acid in 5 ml pyridine and 50 ml dichloromethane was added 2.7 g dicyclohexylcarbodiimide (13 mmole). After stirring the mixture for 24 h at reflux, the solids were filtered off and washed thoroughly with dichloromethane. The filtrate was evaporated to yield 1.7 g curcumin-bis-formylaminobutyrate, m.p. 142-147° C. of approx. 80% purity.

Workup

  1. temperatureat reflux
  2. filtrationthe solids were filtered off
  3. washwashed thoroughly with dichloromethane
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e041a4b904bf44e782eaccc6e34c19c1
Source dataset
uspto-grants-2011_08
Patent number
US08003686B2

Reaction notes

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