Dicyclohexylcarbodiimide → HCID 22877918, compound

HRID 1488852Notes

Reaction equation

HRID 1488852 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:34]([O:36][CH2:37][CH:38]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35])[C@H:25]([C:31](O)=[O:32])[CH2:26][O:27]C(C)=O.C1CCC([N:57]=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.C(OCC)(=O)C.O>[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:34]([NH:24][C@H:25]([C:31]([NH2:57])=[O:32])[CH2:26][OH:27])([O:36][CH2:37][CH:38]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44]2[C:39]1=[CH:40][CH:41]=[CH:42][CH:43]=2)=[O:35]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7018824Fmoc-L-Ser(Ac)HCID 9796936AC-7739 free base

Product 1

HCID 22877918HCID 22877918, compoundYield 64.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Z)-1-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene (1.5 g, 4.76 mmols), 2.1 g (5.7 mmols) of Fmoc-L-Ser(Ac), 1.2 g (5.7 mmols) of DCC and 0.87 g (5.7 mmols) of HOBt.H2O were dissolved in 30 ml of N,N-dimethylformamide, and the mixture was reacted at room temperature for 5 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 1.96 g of the final product in a yield of 61.8%.

Workup

  1. customthe mixture was reacted at room temperature for 5 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-02106b6f62a344f6802fc673c45b207d
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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