Dicyclohexylcarbodiimide → HCID 22877917, compound

HRID 1488850Notes

Reaction equation

HRID 1488850 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH:24]([C:33]([O:35][CH2:36][CH:37]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C@H:25]([C:30]([OH:32])=O)[CH2:26][CH:27]([CH3:29])[CH3:28].C1CCC([N:56]=C=NC2CCCCC2)CC1>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:33]([NH:24][C@H:25]([C:30]([NH2:56])=[O:32])[CH2:26][CH:27]([CH3:29])[CH3:28])([O:35][CH2:36][CH:37]1[C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:44]2[C:49]1=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:34]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1549133Fmoc-leucineHCID 9796936AC-7739 free base

Product 1

HCID 22877917HCID 22877917, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Z)-1-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene (1.92 g, 6.1 mmols), 2.58 g (7.3 mmols) of Fmoc-L-Leu, 1.5 g (7.3 mmols) of DCC and 1.1 g (7.3 mmols) of HOBtH2O were dissolved in 40 ml of N,N-dimethylformamide, and the mixture was reacted at room temperature for 12 hours. The reaction mixture was diluted with ethyl acetate, then filtered and concentrated. The product was purified through silica-gel column chromatography (mixture of ethyl acetate and hexane at a ratio by volume of 1:2) to produce 3.05 g of the final product in a yield of 76.9%.

Workup

  1. customthe mixture was reacted at room temperature for 12 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe product was purified through silica-gel column chromatography (
  5. additionmixture of ethyl acetate and hexane at a ratio by volume of 1:2)

Sources & evidence

ORD record
ord-273ec65a91334d58a45514ce365bf6a2
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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