1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → methyl (2E)-7-(2,3-diphenylacrylamido)heptanoate

HRID 444727

Reaction equation

HRID 444727 reaction equation
[C:1]1(/[C:7](=[CH:11]\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[C:1]1(/[C:7](=[CH:11]\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:8]([NH:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([O:19][CH3:18])=[O:28])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 700620alpha-Phenylcinnamic acid, (E)-HCID 11084159Methyl 7-aminoheptanoate

Product 1

HCID 59475032methyl (2E)-7-(2,3-diphenylacrylamido)heptanoateYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-2,3-diphenylacrylic acid (0.32 g, 1.4 mmol) (prepared according to procedure given in example 1) in DMF (5 mL) was added Methyl-7-aminoheptanoate (0.25 g, 1.3 mmol), EDCI (0.55 g, 2.8 mmol) and HOBt (0.19 g, 1.4 mmol). TEA (0.6 mL, 4.3 mmol) was added dropwise with constant stirring to the above reaction mixture and it was stirred for 2 hours at room temperature. Reaction mixture was diluted with water (100 mL), extracted with ethyl acetate (2×100 mL). The organic layer was washed successively with water (3×50 mL), and brine solution (1×50 mL). The organic layer was dried over Na2SO4 and concentrated to afford the title compound (0.4 g, 61% yield).

Workup

  1. stirringwas stirred for 2 hours at room temperature
  2. customReaction mixture
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. washThe organic layer was washed successively with water (3×50 mL), and brine solution (1×50 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eb66bcd46c0c48cc9358b3ef502ddd39
Source dataset
uspto-grants-2013_07
Patent number
US08476255B2

Linked notes

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