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

HRID 444727
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인쇄 미리보기

반응식

HRID 444727 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb66bcd46c0c48cc9358b3ef502ddd39
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476255B2

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